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4-Cumylphenol

PubChem CID
11742
Structure
4-Cumylphenol_small.png
4-Cumylphenol_3D_Structure.png
4-Cumylphenol__Crystal_Structure.png
Molecular Formula
Synonyms
  • 4-Cumylphenol
  • 599-64-4
  • p-Cumylphenol
  • 4-(2-phenylpropan-2-yl)phenol
  • 4-alpha-Cumylphenol
Molecular Weight
212.29 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04
Description
P-Cumylphenol is a diarylmethane.
4-Cumylphenol has been reported in Panax ginseng with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Cumylphenol.png

1.2 3D Conformer

1.3 Crystal Structures

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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-(2-phenylpropan-2-yl)phenol
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C15H16O/c1-15(2,12-6-4-3-5-7-12)13-8-10-14(16)11-9-13/h3-11,16H,1-2H3
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

QBDSZLJBMIMQRS-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC(C)(C1=CC=CC=C1)C2=CC=C(C=C2)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H16O
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

599-64-4

2.3.2 Deprecated CAS

28261-59-8

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

4-cumylphenol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
212.29 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
3.7
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
212.120115130 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
212.120115130 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
20.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
16
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
207
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Dry Powder; Liquid; Other Solid
White to tan solid; [HSDB] Off-white powder; [Alfa Aesar MSDS]

3.2.2 Color / Form

White to tan crystals
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 351
Prisms from petroleum ether
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-368

3.2.3 Odor

Characteristic phenol odor
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 351

3.2.4 Boiling Point

335 °C
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-368

3.2.5 Melting Point

74.5 °C
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-368

3.2.6 Density

1.115 g/mL at 25 °C
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 351

3.2.7 Vapor Pressure

0.000025 [mmHg]
2.5X10-5 mm Hg at 25 °C (extrapolated)
Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1996)

3.2.8 Decomposition

When heated to decomposition it emits acrid acid and irritating vapors.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1013

3.2.9 Kovats Retention Index

Semi-standard non-polar
1860

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Semi-Volatile Organic Compound (SVOC) and(or) Waste-water effluent contaminant

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.4.2 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.4.3 Polymers

Plastics & Rubber -> Epoxy Resins

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
Calbiochem, Los Angeles, California
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Calbiochem, Los Angeles, California
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

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NIST Number
278584
Library
Main library
Total Peaks
101
m/z Top Peak
197
m/z 2nd Highest
212
m/z 3rd Highest
103
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2 of 4
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NIST Number
72193
Library
Replicate library
Total Peaks
42
m/z Top Peak
197
m/z 2nd Highest
212
m/z 3rd Highest
91
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4.2.2 Other MS

Other MS
MASS: 72193 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)

4.3 IR Spectra

IR Spectra
IR: 1100 (Coblentz Society Spectral Collection)

4.3.1 FTIR Spectra

1 of 2
Technique
Molten layer on KBr pellet (partially recrystallized)
Source of Sample
Huels AG, Marl
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker IFS 85
Technique
Film
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
C87800
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
Vapor Phase
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
C87800
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Use and Manufacturing

7.1 Uses

Sources/Uses
Used to make resins, insecticides, lubricants, polycarbonates, and surfactants; [HSDB] Used as an intermediate; [ECHA REACH Registrations]
Intermediate for resins, insecticides, lubricants
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 351
The major use of phenol, 4-(1-methyl-1-phenethyl)- (which is commonly known as 4-cumylphenol) is as a chain terminator for polycarbonates ... Other uses include the production of phenolic resins, some of which have applications in the electronics industry; another application involves its reaction with ethylene oxide to form a specialty surfactant.
Lorenc JF et al; Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2012). New York, NY: John Wiley & Sons; Alkylphenols. Online Posting Date: Sept 19, 2003
... p-Cumylphenol can be condensed with formaldehyde to give acid- and base-resistant resins. p-Cumylphenol of high purity ... serves as a molecular-mass controlling component in the production of polycarbonates.
Fiege H et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2012). NY, NY: John Wiley & Sons; Phenol Derivatives. Online Posting Date: June 15, 2000

7.1.1 Industry Uses

  • Terminator/Blocker
  • Intermediates
  • Intermediate

7.1.2 Consumer Uses

Intermediates

7.2 Methods of Manufacturing

p-Cumylphenol is formed to a certain extent during acid-catalyzed cleavage of cumene hydroperoxide. The high boiling still bottoms of phenol-acetone plants are a potential source for this aralkylphenol, which is, however, not exploited.
Fiege H et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2012). NY, NY: John Wiley & Sons; Phenol Derivatives. Online Posting Date: June 15, 2000

7.3 U.S. Production

Aggregated Product Volume

2019: 20,000,000 lb - <100,000,000 lb

2018: 20,000,000 lb - <100,000,000 lb

2017: 20,000,000 lb - <100,000,000 lb

2016: 20,000,000 lb - <100,000,000 lb

Phenol, 4-(1-methyl-1-phenylethyl)- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Phenol, 4-(1-methyl-1-phenylethyl)- (599-64-4). Available from, as of October 18, 2012: https://www.epa.gov/hpv/pubs/general/opptsrch.htm
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
>1 million - 10 million
Year
1990
Production Range (pounds)
>10 million - 50 million
Year
1994
Production Range (pounds)
>10 million - 50 million
Year
1998
Production Range (pounds)
>10 million - 50 million
Year
2002
Production Range (pounds)
>10 million - 50 million
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Phenol, 4-(1-methyl-1-phenylethyl)- (599-64-4). Available from, as of October 18, 2012: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Phenol, 4-(1-methyl-1-phenylethyl)-. Aggregated National Production Volume: 10 to < 50 million pounds.
US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. Phenol, 4-(1-methyl-1-phenylethyl)- (599-64-4). Available from, as of October 18, 2012: https://cfpub.epa.gov/iursearch/index.cfm?s=chem&err=t

7.4 General Manufacturing Information

Industry Processing Sectors
  • Petroleum Refineries
  • Plastics Material and Resin Manufacturing
EPA TSCA Commercial Activity Status
Phenol, 4-(1-methyl-1-phenylethyl)-: ACTIVE

8 Identification

8.1 Analytic Laboratory Methods

Method: USGS-NWQL O-1433-01; Procedure: gas cromatography/mass spectrometry; Analyte: 4-cumylphenol; Matrix: filtered wastewater and natural-water samples; Detection Limit: 0.37 ug/L.
National Environmental Methods Index; Analytical, Test and Sampling Methods. 4-Cumylphenol (599-64-4). Available from, as of October 19, 2012: https://www.nemi.gov

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

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Note
Pictograms displayed are for 99.6% (233 of 234) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 0.4% (1 of 234) of reports.
Pictogram(s)
Corrosive
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H302 (48.7%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (47.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (51.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (49.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H373 (46.2%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H400 (48.3%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (47.9%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 234 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 234 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 16 notifications provided by 233 of 234 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (48.7%)

Skin Irrit. 2 (50%)

Eye Dam. 1 (47.9%)

Eye Irrit. 2A (51.3%)

STOT SE 3 (49.6%)

STOT RE 2 (46.2%)

Aquatic Acute 1 (48.3%)

Aquatic Chronic 1 (47.9%)

Acute toxicity (Oral) - Category 4

Reproductive toxicity - Category 2

Specific target organ toxicity - Repeated exposure - Category 2 (kidney)

Hazardous to the aquatic environment (Acute) - Category 2

Hazardous to the aquatic environment (Long-term) - Category 2

9.1.3 Hazards Summary

May cause serious eye injury; Harmful by ingestion; [ECHA REACH Registrations] A skin and strong eye irritant; [Alfa Aesar MSDS] See Bisphenol A.

9.2 Accidental Release Measures

9.2.1 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

9.3 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Phenol, 4-(1-methyl-1-phenylethyl)-
REACH Registered Substance

10 Toxicity

10.1 Toxicological Information

10.1.1 USGS Health-Based Screening Levels for Evaluating Water-Quality

Chemical
4-Cumylphenol
Chemical Classes
Semi-Volatile Organic Compound (SVOC) and(or) Waste-water effluent contaminant
Reference
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

10.1.2 Acute Effects

10.1.3 Toxicity Data

LCLo0 (rat) = 72 mg/m3

10.1.4 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

10.1.5 Human Toxicity Excerpts

/ENDOCRINE MODULATION/ A receptor-binding assay and X-ray crystal structure analysis demonstrated that the endocrine disruptor bisphenol A (BPA) strongly binds to human estrogen-related receptor gamma (ERRgamma). BPA is well anchored to the ligand-binding pocket, forming hydrogen bonds with its two phenol-hydroxyl groups. In this study, /the researchers/ found that 4-alpha-cumylphenol lacking one of its phenol-hydroxyl groups also binds to ERRgamma very strongly. The 2.0 A crystal structure of the 4-alpha-cumylphenol/ERRgamma complex clearly revealed that ERRgamma's Leu345-beta-isopropyl plays a role in the tight binding of 4-alpha-cumylphenol and BPA, rotating in a back-and-forth induced-fit manner. PMID:18582436
Matsushima A et al; Biochem Biophys Res Commun 373 (3): 408-13 (2008)

10.1.6 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Five groups of male and female Sprague-Dawley rats were given oral doses of phenol, 4-(1-methyl-1-phenylethyl)-. The test material was prepared as a 25% w/v formulation in corn oil. Four dose levels were evaluated: 5.0, 2.5, 1.25 and 0.625 g/kg. Animals were observed for 14 days. Clinical signs: Brownish red and saliva like stains on muzzle, fecal stains, piloerection, unkempt fur, moderate and/or slight depression, extensive yellow brown stains on anal and stomach area, red stains around eyes and hunched posture were noted in the two highest dose levels. Red stains on muzzle, piloerection, slight depression, fecal and urine stains, brown yellow stains on urogenital area, rapid breathing and unkempt fur were seen in animals dosed at 1.25 or 0.625 g/kg. Number of deaths at each dose level: At the dose level of 5.0 g/kg four deaths (100%), were noted between days one and two of the observation period. At the dose level of 2.5 g/kg four deaths (100%), were noted between days one and five of the observation period. At the dose level of 1.25 g/kg no deaths (0%), were noted during the observation period. At the dose level of 0.625 g/kg no deaths (0%), were noted during the observation period.
EPA/Office of Pollution Prevention and Toxics; High Production Volume Information System (HPVIS) on Phenol, 4-(1-methyl-1-phenylethyl)- (599-64-4). Available from, as of November 12, 2012: https://www.epa.gov/hpvis/index.html
/ENDOCRINE MODULATION/ The estrogenic activities of 13 Bisphenol-A (BPA)-related chemicals for development of new polymers by three in vitro bioassay have been examined in the presence and absence of a post-mitochondrial metabolizing system (S9 mix). BPA, Bisphenol-B (BPB), Bisphenol-F (BPF), Bisphenol-S (BPS), 4,4-ethylidenebisphenol (BP1), 4,4-dihydroxybenzophenone (BP2), 2,2-bis (4-hydroxyphenyl)-hexafluoropropane (BP3), 4,4-(1,4-phenylenediisopropylidene) bisphenol (BP4), 4,4-cyclohexylidenebisphenol (BP5), 4,4-dihydroxydiphenyl ether (BP6), 4-hydroxydiphenylmethane (BP7), 4-cumylphenol (BP8) and 4,4-dihydroxydiphenyl sulfide (BP9) were each diluted with dimethyl sulfoxide to final concentrations ranging from 1x10-7 to 1x10-3 M in both the yeast two-hybrid system and in a fluorescence polarization system. Dilutions of 1x10-9 to 1x10-4 M were assayed in the E-screen, respectively. Except for BPS and BP4, the chemicals tested showed estrogenic activity in the absence of cut S9 mix preparation and the activity was enhanced with S9 mix. BPS, which was initially negative, was active with S9 mix in the yeast two-hybrid system. BP2 was weakly estrogenic with or without S9 mix. Chemicals other than BP2 were positive in the competition binding assay. All chemicals tested showed estrogenic activity in the E-screen, the concentration level of which was1x 10+4 times lower than those of the other two assays.
Hashimoto Y et al; Toxicol In Vitro 15 (4-5): 421-5 (2001)
/GENOTOXICITY/ The mutagenicity potential of p-(alpha, alpha-dimethylbenzyl)phenol was evaluated in vitro in S. typhimurium (TA 100, TA1535, TA98, TA 1538 and TA1537) in the presence and absence of metabolic activation up to 500 ug/plate of test substance. No increases in mutation frequency were reported at any concentration tested with or without metabolic activation. Cytotoxicity was observed at concentrations greater than ug/plate with metabolic activation and greater than 50 ug/plate without metabolic activation.
USEPA; Hazard Characterization Document, Alkylphenols Category, p30 (September 2009). Available from, as of November 30, 2012: https://www.epa.gov/hpvis/hazchar/Category_Alkylphenols_Sept2009.pdf

10.1.7 Non-Human Toxicity Values

LD50 Rat oral 1770 mg/kg bw
EPA/Office of Pollution Prevention and Toxics; High Production Volume Information System (HPVIS) on Phenol, 4-(1-methyl-1-phenylethyl)- (599-64-4). Available from, as of October 31, 2012: https://www.epa.gov/hpvis/index.html
LD50 Frog oral 335 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1013

10.2 Ecological Information

10.2.1 Environmental Fate / Exposure Summary

Phenol, 4-(1-methyl-1-phenethyl)-'s production and use as an intermediate for resins, insecticides and lubricants) and its major use as a chain terminator for polycarbonates may result in its release to the environment through various waste streams. If released to air, an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C indicates phenol, 4-(1-methyl-1-phenethyl)- will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase phenol, 4-(1-methyl-1-phenethyl)- will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 9 hours. Particulate-phase phenol, 4-(1-methyl-1-phenethyl)- will be removed from the atmosphere by wet and dry deposition. If released to soil, phenol, 4-(1-methyl-1-phenethyl)- is expected to have no mobility based upon an estimated Koc of 2.9X10+9. The estimated pKa of phenol, 4-(1-methyl-1-phenethyl)- is 10.0, indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 8.8X10-8 atm-cu m/mole. Phenol, 4-(1-methyl-1-phenethyl)- is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks suggests that biodegradation is not an important environmental fate process in soil or water. If released into water, phenol, 4-(1-methyl-1-phenethyl)- is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 240 suggests the potential for bioconcentration in aquatic organisms is high; however, BCF test results in catfish suggest low bioconcetration. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Photo-oxidation may have some importance as a fate process in natural water exposed to sunlight. Occupational exposure to phenol, 4-(1-methyl-1-phenethyl)- may occur through inhalation and dermal contact with this compound at workplaces where phenol, 4-(1-methyl-1-phenethyl)- is produced or used. (SRC)

10.2.2 Artificial Pollution Sources

Phenol, 4-(1-methyl-1-phenethyl)-'s production and use as an intermediate for resins, insecticides and lubricants(1) and its major use as a chain terminator for polycarbonates(2) may result in its release to the environment through various waste streams(SRC). Another application involves its reaction with ethylene oxide to form a specialty surfactant(2); it has been reported to be a detergent metabolite(3).
(1) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary. 15th ed., New York, NY: John Wiley & Sons, Inc., p. 351 (2007)
(2) Lorenc JF et al; Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2012). New York, NY: John Wiley & Sons; Alkylphenols. Online Posting Date: Sept 19, 2003
(3) Kolpin DW et al; Sci Total Environ 348: 119-130 (2004)

10.2.3 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+4(SRC), determined from a structure estimation method(2), indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to be immobile in soil(SRC). The estimated pKa of phenol, 4-(1-methyl-1-phenethyl)- is 10.0(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of phenol, 4-(1-methyl-1-phenethyl)- from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(5). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.10. Jan, 2011. Available from, as of Oct 30, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) SPARC; pKa/property server. Ver 4.6., Oct, 2011. Available from, as of Oct 30, 2012: https://archemcalc.com/sparc/
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(5) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1996)
(6) Sedkyh A, Klopman G; SAR QSAR Environ Res 18: 693-709 (2007)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+5(SRC), determined from a structure estimation method(2), indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 240(SRC), from an estimated log Kow of 4.12(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, phenol, 4-(1-methyl-1-phenethyl)- is reported to have low bioconcentration based on test results using catfish(5). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6)suggests that biodegradation is not an important environmental fate process in water(SRC). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy radicals with half-lives on the order of days to weeks at the water surface(7); therefore, photo-oxidation may have some importance as a fate process for phenol, 4-(1-methyl-1-phenethyl)- in natural water(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.10. Jan, 2011. Available from, as of Oct 30, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)
(5) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech Eval. Available from, as of Oct 30, 2012: https://www.safe.nite.go.jp/english/db.html
(6) Sedkyh A, Klopman G; SAR QSAR Environ Res 18: 693-709 (2007)
(7) Mill T, Mabey W; p. 209 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenol, 4-(1-methyl-1-phenethyl)-, which has an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phenol, 4-(1-methyl-1-phenethyl)- is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 9 hours(SRC), calculated from its rate constant of 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase phenol, 4-(1-methyl-1-phenethyl)- may be removed from the air by wet and dry deposition(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1996)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.10. Jan, 2011. Available from, as of Oct 30, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm

10.2.4 Environmental Biodegradation

AEROBIC: Phenol, 4-(1-methyl-1-phenethyl)-, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1).
(1) Sedkyh A, Klopman G; SAR QSAR Environ Res 18: 693-709 (2007)

10.2.5 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of phenol, 4-(1-methyl-1-phenethyl)- with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy (RO2) radicals with half-lives on the order of days to weeks at the water surface(3); therefore, photo-oxidation may have some importance as a fate process for phenol, 4-(1-methyl-1-phenethyl)- in natural water(SRC).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.10. Jan, 2011. Available from, as of Oct 30, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
(3) Mill T, Mabey W; p. 209 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)

10.2.6 Environmental Bioconcentration

An estimated BCF of 240 was calculated in fish for phenol, 4-(1-methyl-1-phenethyl)-(SRC), using an estimated log Kow of 4.12(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, phenol, 4-(1-methyl-1-phenethyl)- is reported to have low bioconcentration based on test results using catfish(3).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.10. Jan, 2011. Available from, as of Oct 30, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Franke C et al; Chemosphere 29: 1501-14 (1994)
(3) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech Eval. Available from, as of Oct 30, 2012: https://www.safe.nite.go.jp/english/db.html

10.2.7 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of phenol, 4-(1-methyl-1-phenethyl)- can be estimated to be 2.9X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that phenol, 4-(1-methyl-1-phenethyl)- is expected to be immobile in soil. The estimated pKa of phenol, 4-(1-methyl-1-phenethyl)- is 10.0(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.10. Jan, 2011. Available from, as of Oct 30, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) SPARC; pKa/property server. Ver 4.6., Oct, 2011. Available from, as of Oct 30, 2012: https://archemcalc.com/sparc/
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

10.2.8 Volatilization from Water / Soil

The Henry's Law constant for phenol, 4-(1-methyl-1-phenethyl)- is estimated as 8.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to be essentially non-volatile from water surfaces(2). Phenol, 4-(1-methyl-1-phenethyl)-'s Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(3).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.10. Jan, 2011. Available from, as of Oct 30, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1996)

10.2.9 Environmental Water Concentrations

SURFACE WATER: Phenol, 4-(1-methyl-1-phenethyl)- was not detected (reporting limit of 1 ug/L) in 76 samples water samples collected upstream and downstream from selected towns and cities in Iowa in 2001(1). Phenol, 4-(1-methyl-1-phenethyl)- concentrations of 0.016 to 0.053 were quantified in three water samples collected from the Rhine River delta, The Netherlands in 1989(2).
(1) Kolpin DW et al; Sci Total Environ 348: 119-130 (2004)
(2) Hendriks AJ et al; Water Res 28: 581-598 (1994)

10.2.10 Effluent Concentrations

A phenol, 4-(1-methyl-1-phenethyl)- concentration of <0.01 to 0.49 ug/L was detected in the manifold exhaust gases from a polycarbonate processing extruder inside a polycarbonate processing facility(1).
(1) Rhodes VL et al; J Air Waste Manage Assoc 52: 781-788 (2002)

10.2.11 Probable Routes of Human Exposure

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of phenol, 4-(1-methyl-1-phenethyl)- is 1000 or greater; the data may be greatly underestimated(1).
(1) US EPA; Inventory Update Reporting (IUR). Non-confidential 2006 IUR Records by Chemical, including Manufacturing, Processing and Use Information. Washington, DC: U.S. Environmental Protection Agency. Available from, as of Oct 30, 2012: https://cfpub.epa.gov/iursearch/index.cfm
Occupational exposure to phenol, 4-(1-methyl-1-phenethyl)- may occur through inhalation and dermal contact with this compound at workplaces where phenol, 4-(1-methyl-1-phenethyl)- is produced or used. Since phenol, 4-(1-methyl-1-phenethyl)- has been identified as a detergent metabolite(1), the general population may be exposed via dermal contact with wastewaters or surface waters containing phenol, 4-(1-methyl-1-phenethyl)-(SRC).
(1) Kolpin DW et al; Sci Total Environ 348: 119-130 (2004)

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 ChEMBL Target Tree

17.5 UN GHS Classification

17.6 NORMAN Suspect List Exchange Classification

17.7 EPA DSSTox Classification

17.8 EPA TSCA and CDR Classification

17.9 LOTUS Tree

17.10 EPA Substance Registry Services Tree

17.11 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    https://www.epa.gov/chemical-data-reporting
  7. EPA Chemicals under the TSCA
    Phenol, 4-(1-methyl-1-phenylethyl)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  9. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
    4-(α,α-dimethylbenzyl)phenol
    https://chem.echa.europa.eu/100.009.063
  10. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. Hazardous Substances Data Bank (HSDB)
    Phenol, 4-(1-methyl-1-phenethyl)-
    https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8089
  12. BindingDB
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  17. Crystallography Open Database (COD)
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    https://creativecommons.org/publicdomain/zero/1.0/
  18. The Cambridge Structural Database
  19. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    https://haz-map.com/About
  20. NITE-CMC
    4-(2-Phenylpropan-2-yl)phenol - FY2012 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/12-mhlw-0135e.html
  21. Japan Chemical Substance Dictionary (Nikkaji)
  22. KEGG
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  23. Natural Product Activity and Species Source (NPASS)
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    https://www.nist.gov/srd/public-law
    Phenol, 4-(1-methyl-1-phenylethyl)-
    http://www.nist.gov/srd/nist1a.cfm
  26. SpectraBase
    Phenol, 4-(1-methyl-1-phenylethyl)-
    https://spectrabase.com/spectrum/7n00LYgZzVg
    4-(1-Methyl-1-phenylethyl)phenol
    https://spectrabase.com/spectrum/2pRB7Yyw5Wy
    p-(alpha,alpha-DIMETHYLBENZYL)PHENOL
    https://spectrabase.com/spectrum/1wv0M12FYJE
    p-(alpha,alpha-dimethylbenzyl)phenol
    https://spectrabase.com/spectrum/Cu8YcphgWta
    p-(alpha,alpha-dimethylbenzyl)phenol
    https://spectrabase.com/spectrum/5tTAXlyaG7z
    PHENOL, P-/A,A-DIMETHYLBENZYL/-,
    https://spectrabase.com/spectrum/ImOAf32ibKc
    2-(4-Hydroxyphenyl)-2-phenylpropane
    https://spectrabase.com/spectrum/r1AsHsspTC
  27. NORMAN Suspect List Exchange
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    4-Cumylphenol
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    https://www.norman-network.com/nds/SLE/
  28. Protein Data Bank in Europe (PDBe)
  29. RCSB Protein Data Bank (RCSB PDB)
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  30. Springer Nature
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  32. Thieme Chemistry
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  36. Medical Subject Headings (MeSH)
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  37. GHS Classification (UNECE)
  38. EPA Substance Registry Services
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
CONTENTS