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2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-

PubChem CID
1712087
Structure
2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-_small.png
2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-_3D_Structure.png
Molecular Formula
Synonyms
  • 3033-23-6
  • (-)-cis-rose oxide
  • 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-
  • Rose oxide, cis-(-)-
  • (2S,4R)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran
Molecular Weight
154.25 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-12
  • Modify:
    2025-01-18
Description
(2S,4R)-rose oxide is a rose oxide that has S configuration at position 2 and R configuration at position 4. Also known as (-)-cis-rose oxide, it is responsible for the characteristic fragrance of roses. It has a role as a fragrance and a plant metabolite. It is an enantiomer of a (2R,4S)-rose oxide.
(2S,4R)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran has been reported in Swertia japonica, Cryptomeria japonica, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,4R)-4-methyl-2-(2-methylprop-1-enyl)oxane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

CZCBTSFUTPZVKJ-NXEZZACHSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@@H]1CCO[C@@H](C1)C=C(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H18O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

3033-23-6
876-17-5

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
154.25 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.9
Reference
Computed by XLogP3 3.0 (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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
154.135765193 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
154.135765193 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
9.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
145
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
2
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 Chemical Classes

3.2.1 Fragrances

Fragrance Ingredient (Rose oxide levo) -> IFRA transparency List

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80B
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

139 99.99

69 54.50

41 31.80

55 26.85

83 25.99

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License
CC BY-NC-SA
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Source of Spectrum
AJ-63-1909-15
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Food Additive Classes

Flavoring Agents

8 Use and Manufacturing

8.1 Uses

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

8.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients

8.1.2 Household Products

Household & Commercial/Institutional Products

Information on 15 consumer products that contain Laevo-Rose Oxide in the following categories is provided:

• Auto Products

• Inside the Home

8.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

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Note
Pictograms displayed are for > 99.9% (1051 of 1052) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1052) of reports.
Pictogram(s)
Irritant
Health Hazard
Signal
Warning
GHS Hazard Statements

H315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (> 99.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H361 (90.4%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statement Codes

P203, P264, P264+P265, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P337+P317, P362+P364, 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 1052 reports by companies from 6 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 1052 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 5 notifications provided by 1051 of 1052 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

Skin Irrit. 2 (> 99.9%)

Eye Irrit. 2 (> 99.9%)

Repr. 2 (90.4%)

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

STOT SE 3 (100%)

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2S-cis)-
New Zealand EPA Inventory of Chemical Status
2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2S,4R)-: Does not have an individual approval but may be used under an appropriate group standard

9.3 Other Safety Information

Chemical Assessment
IMAP assessments - 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2S-cis)-: Environment tier I assessment

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Chemical Co-Occurrences in Literature

10.4 Chemical-Gene Co-Occurrences in Literature

10.5 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

12 Taxonomy

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

13 Classification

13.1 ChEBI Ontology

13.2 ChemIDplus

13.3 UN GHS Classification

13.4 EPA CPDat Classification

13.5 NORMAN Suspect List Exchange Classification

13.6 EPA DSSTox Classification

13.7 Consumer Product Information Database Classification

13.8 EPA TSCA and CDR Classification

13.9 LOTUS Tree

13.10 EPA Substance Registry Services Tree

13.11 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2S-cis)-
    https://services.industrialchemicals.gov.au/search-assessments/
    2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2S-cis)-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA Chemicals under the TSCA
    2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    (2S,4R)-4-Methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran
    https://comptox.epa.gov/dashboard/DTXSID6051980
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (2S-cis)-tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran
    https://echa.europa.eu/substance-information/-/substanceinfo/100.019.290
    rac-(2R,4S)-4-methyl-2-(2-methylprop-1-en-1-yl)oxane
    https://echa.europa.eu/substance-information/-/substanceinfo/100.112.087
    (2S-cis)-tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran (EC: 221-217-9)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/84407
    rac-(2R,4S)-4-methyl-2-(2-methylprop-1-en-1-yl)oxane (EC: 618-036-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/28519
  7. 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
  8. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  9. 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/
  10. ChEBI
  11. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    (2S,4R)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran
    https://www.wikidata.org/wiki/Q27162308
  12. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  13. EPA Chemical and Products Database (CPDat)
    (2S,4R)-4-Methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran
    https://comptox.epa.gov/dashboard/DTXSID6051980#exposure
  14. EU Food Improvement Agents
    2S-cis-Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran
    https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32012R0872
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. 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
  17. SpectraBase
    (2S,4R)-4-methyl-2-(2-methylprop-1-enyl)oxane
    https://spectrabase.com/spectrum/6xAb2FvXZcr
    (2S,4R)-4-methyl-2-(2-methylprop-1-enyl)oxane
    https://spectrabase.com/spectrum/3u9zkVeqL23
  18. NMRShiftDB
  19. Springer Nature
  20. Wikidata
  21. PubChem
  22. GHS Classification (UNECE)
  23. 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/
  24. EPA Substance Registry Services
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  26. PATENTSCOPE (WIPO)
CONTENTS