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Sodium tetradecyl sulfate

PubChem CID
23665770
Structure
Sodium tetradecyl sulfate_small.png
Sodium tetradecyl sulfate_3D_Structure.png
Molecular Formula
Synonyms
  • sodium tetradecyl sulfate
  • 1191-50-0
  • Sodium myristyl sulfate
  • Niaproof 4
  • Tetradecyl sodium sulfate
Molecular Weight
316.43 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2008-02-05
  • Modify:
    2025-01-04
Description
An anionic surface-active agent used for its wetting properties in industry and used in medicine as an irritant and sclerosing agent for hemorrhoids and varicose veins.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Sodium tetradecyl sulfate.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;tetradecyl sulfate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C14H30O4S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-19(15,16)17;/h2-14H2,1H3,(H,15,16,17);/q;+1/p-1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

UPUIQOIQVMNQAP-UHFFFAOYSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C14H29NaO4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1191-50-0
139-88-8

2.3.2 Deprecated CAS

22088-37-5, 2460408-23-3

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Sodium Tetradecyl Sulfate
  • Sotradecol
  • Sotradecol Sodium
  • Sulfate, Sodium Tetradecyl
  • Tergitol 4
  • Tetradecyl Sulfate, Sodium
  • Trombavar
  • Trombovar

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
316.43 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
14
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
316.16842486 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
316.16842486 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
74.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
275
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
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
2
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 Collision Cross Section

195.8 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Sclerosing Solutions; Sclerotherapies; Surface-Active Agents
Human drug -> Prescription; Active ingredient (SODIUM TETRADECYL SULFATE)

3.3.2 Cosmetics

Cosmetic ingredients (Sodium Myristyl Sulfate) -> CIR (Cosmetic Ingredient Review)
Emulsifying; Cleansing; Surfactant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.3.3 Surfactants

Surfactant
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Source of Sample
Eastman Organic Chemicals, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+NH4]+
Precursor m/z
334.2022399902344
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
positive
Collision Energy
65HCD
Top 5 Peaks

91.054216 100

119.085573 72.58

58.065386 33.52

92.057556 12.59

117.069891 12.12

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2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+NH4]+
Precursor m/z
334.2022399902344
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
positive
Collision Energy
45HCD
Top 5 Peaks

119.085557 100

91.054231 60.13

58.065389 30.65

120.088889 15.93

240.268529 13.75

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4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
BETWEEN SALTS
Source of Sample
Niacet Corporation
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Technique
BETWEEN SALTS
Source of Sample
Niacet Corporation
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
293938
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 Drug and Medication Information

7.1 Drug Indication

For the treatment of small uncomplicated varicose veins of the lower extremities that show simple dilation with competent valves.

7.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Sclerosing Solutions; Sclerotherapies; Surface-Active Agents

7.3 FDA Approved Drugs

7.4 FDA Orange Book

7.5 FDA National Drug Code Directory

7.6 Drug Labels

Drug and label
Active ingredient and drug

7.7 Clinical Trials

7.7.1 ClinicalTrials.gov

7.7.2 EU Clinical Trials Register

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Sodium tetradecyl sulfate is an anionic surfactant which occurs as a white, waxy solid. It is used as a sclerosing agent in sclerotherapy. Sclerotherapy is an injection of a sclerosing agent directly through the skin into a lesion and is used primarily for slow-flow vascular anomalies, particularly for venous malformation and lymphatic malformation. Intravenous injection causes intima inflammation and thrombus formation. This usually occludes the injected vein. Subsequent formation of fibrous tissue results in partial or complete vein obliteration that may or may not be permanent.

8.2 MeSH Pharmacological Classification

Sclerosing Solutions
Chemical agents injected into blood vessels and lymphatic sinuses to shrink or cause localized THROMBOSIS; FIBROSIS, and obliteration of the vessels. This treatment is applied in a number of conditions such as VARICOSE VEINS; HEMORRHOIDS; GASTRIC VARICES; ESOPHAGEAL VARICES; PEPTIC ULCER HEMORRHAGE. (See all compounds classified as Sclerosing Solutions.)
Surface-Active Agents
Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)

8.3 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

C05B - Antivaricose therapy

C05BB - Sclerosing agents for local injection

C05BB04 - Sodium tetradecyl sulfate

8.4 Mechanism of Action

Sodium tetradecyl sulfate is a potent toxin for endothelial cells in that brief exposure to even low concentrations are effective in stripping endothelium over a considerable distance and exposing highly thrombogenic endothelium in the process. Diluted sodium tetradecyl sulfate is also able to induce a hypercoagulable state, possibly by selective inhibition of protein C, and can also promote platelet aggregation.

9 Use and Manufacturing

9.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Sodium Myristyl Sulfate
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

9.1.1 Use Classification

EPA Safer Chemical Functional Use Classes -> Surfactants
Safer Chemical Classes -> Green half-circle Green half-circle - The chemical is expected to be of low concern
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Cosmetics -> Emulsifying; Cleansing; Surfactant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
1-Tetradecanol, 1-(hydrogen sulfate), sodium salt (1:1): ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 EPA Safer Chemical

Chemical: Sodium myristyl sulfate

Green half-circle Green half-circle - The chemical is expected to be of low concern based on experimental and modeled data. Additional data would strengthen EPA's confidence in the chemical's safer status.

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1-Tetradecanol, hydrogen sulfate, sodium salt
New Zealand EPA Inventory of Chemical Status
Sodium tetradecyl sulfate: Does not have an individual approval but may be used under an appropriate group standard

11 Toxicity

11.1 Toxicological Information

11.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the clinical use of sodium tetradecyl sulfate during breastfeeding. Although sodium tetradecyl sulfate is unlikely to adversely affect the breastfed infant, international guidelines recommend that breastfeeding be withheld for 2 days after sclerotherapy.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

11.1.2 Acute Effects

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Wiley References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 WHO ATC Classification System

17.3 EPA Safer Choice

17.4 ChemIDplus

17.5 ChEMBL Target Tree

17.6 UN GHS Classification

17.7 EPA CPDat Classification

17.8 NORMAN Suspect List Exchange Classification

17.9 CCSBase Classification

17.10 EPA DSSTox Classification

17.11 EPA TSCA and CDR Classification

17.12 EPA Substance Registry Services Tree

17.13 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1-Tetradecanol, hydrogen sulfate, sodium salt
    https://services.industrialchemicals.gov.au/search-inventory/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
    Sodium tetradecyl sulfate
    https://www.drugbank.ca/drugs/DB00464
  4. EPA Chemicals under the TSCA
    1-Tetradecanol, 1-(hydrogen sulfate), sodium salt (1:1)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  10. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  11. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  12. Therapeutic Target Database (TTD)
  13. Cosmetic Ingredient Review (CIR)
  14. EPA Chemical and Products Database (CPDat)
  15. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  16. DailyMed
  17. Drugs and Lactation Database (LactMed)
  18. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  19. EPA Safer Choice
    EPA Safer Chemical Ingredients Classification
    https://www.epa.gov/saferchoice
  20. FDA Orange Book
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  21. EU Clinical Trials Register
  22. Japan Chemical Substance Dictionary (Nikkaji)
  23. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  24. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  25. SpectraBase
    SULFURIC ACID, MONOTETRADECYL ESTER, SODIUM SALT
    https://spectrabase.com/spectrum/6xeOXYCng0O
    Tetradecyl sulfate sodium salt
    https://spectrabase.com/spectrum/1nW04AwRNit
  26. Springer Nature
  27. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  28. Wikidata
  29. Wikipedia
  30. Wiley
  31. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  32. PubChem
  33. GHS Classification (UNECE)
  34. EPA Substance Registry Services
  35. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  36. PATENTSCOPE (WIPO)
CONTENTS