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trans-carveol

Chemical Structure

General Material Information

Preferred name trans-carveol
Trivial Name (±)-trans-Carveol
Short Description trans-1-methyl-4-isoprpenyl-6-cyclohexen-2-ol
Formula C10 H16 O
CAS Number 1197-07-5
FDA UNII W241K84ZSQ
Nikkaji Number J9.143J
Beilstein Number 2206715
xLogP3-AA 2.10 (est)
NMR Predictor External link
Synonyms
  • (-)-trans- carveol
  • 2-cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R,5S)-
  • 2-cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, trans-
  • trans-p- mentha-1,8-dien-6-ol
  • trans-para- mentha-1,8-dien-6-ol
  • p- mentha-6,8-dien-2-ol, trans-
  • trans-1-methyl-4-isoprpenyl-6-cyclohexen-2-ol
  • (1S-trans)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol
  • (1S-trans)-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol
  • (1R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
  • (1R,5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
  • (1R,5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
  • 2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R,5S)-rel-
  • p-Mentha-6,8-dien-2-ol, trans-
  • 2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, trans-
  • rel-(1R,5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol
  • trans-Mentha-1,8-dien-6-ol
  • (E)-Carveol
  • (±)-trans-Carveol
  • trans-5-(1-Methylethenyl)-2-methyl-2-cyclohexenol

General Material Description



6R*, trans relative to isopropenyl group

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

Leffingwell:Chirality or Article
(1R,5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):443178
Pubchem (sid):135052075
Flavornet:1197-07-5
Pherobase:View
Publications by PubMed
Chemical composition, cytotoxicity and in vitro antitrypanosomal and antiplasmodial activity of the essential oils of four Cymbopogon species from Benin.
Chemical composition and biological activities of Tunisian Cuminum cyminum L. essential oil: a high effectiveness against Vibrio spp. strains.
Improved reactor performance and operability in the biotransformation of carveol to carvone using a solid-liquid two-phase partitioning bioreactor.
Phosphotungstic acid as a versatile catalyst for the synthesis of fragrance compounds by alpha-pinene oxide isomerization: solvent-induced chemoselectivity.
Enhanced bioproduction of carvone in a two-liquid-phase partitioning bioreactor with a highly hydrophobic biocatalyst.
Inhibitory effects of substrate and product on the carvone biotransformation activity of Rhodococcus erythropolis.
Chemical composition and antimicrobial activity of the essential oil from Ambrosia trifida L.
Regio- and stereoselective fungal oxyfunctionalisation of limonenes.
Analysis of volatile components from Ziziphora taurica subsp. taurica by steam distillation, superheated-water extraction, and direct thermal desorption with GCxGC-TOFMS.
Monoterpene metabolism. Cloning, expression, and characterization of (-)-isopiperitenol/(-)-carveol dehydrogenase of peppermint and spearmint.
Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India).
Volatile chemicals identified in extracts from newly hybrid citrus, dekopon (Shiranuhi mandarin Suppl. J.).
Effects of storage conditions on the composition of Citrus tamurana Hort. ex Tanaka (hyuganatsu) essential oil.
Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes.
Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation.
Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes.
Biotransformation of D-limonene to (+) trans-carveol by toluene-grown Rhodococcus opacus PWD4 cells.
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites.
Functional expression of regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha spp.) in Escherichia coli and saccharomyces cerevisiae.
Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (-)-4S-limonene-3-hydroxylase and (-)-4S-limonene-6-hydroxylase.
Effects of R-(+)-limonene on submerged cultures of the terpene transforming basidiomycete Pleurotus sapidus.
Biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway. I. Demonstration Of enzyme activities and their changes with development
Cytochrome P450 limonene hydroxylases of Mentha species.
Biochemical characterization of a spearmint mutant that resembles peppermint in monoterpene content.
Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.
Biochemical and Histochemical Localization of Monoterpene Biosynthesis in the Glandular Trichomes of Spearmint (Mentha spicata).

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
UM BBD:Search
KEGG (GenomeNet):C11409
HMDB (The Human Metabolome Database):HMDB03450
FooDB:FDB029708
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Specific gravity @ 25 °C
Pounds per Gallon
Boiling Point 231 to 232°C @ 760 mm Hg
Vapor Pressure 0.012 mmHg @ 25 °C
Flash Point TCC Value 91.11 °C TCC
logP (o/w) 2.819 est
Solubility
alcohol Yes
water, 519.7 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Spicy
caraway, solvent, spearmint
General comment At 100.00 %. caraway solvent spearmint

Occurrences

Potential Uses

Applications
Odor purposes Acacia , Allspice , Allspice , Angelica , Arnica flower , Bay rum , Bayberry , Bayberry , Beeswax absolute replacer , Calamus oil replacer , Caraway seed , Cardamom oil replacer , Carnation , Carrot seed , Cassia , Cassia blossom , Chamomile , Cinnamon , Clary sage oil replacer , Clove , Copaiba balsam , Coriander , Croton eluteria bark , Cumin oil replacer , Currant bud absolute replacer , Curry leaf , Cypress oil replacer , Dill weed , Dogwood , Elder flower , Galangal root , Geranium , Ginger , Ginger white ginger , Gingerbread , Graham cracker , Guaiacwood , Habuba , Hinoki oil replacer , Hollyberry , Hop , Jonquil , Mace , Maja , Marjoram , Mimosa , Myrrh , Nutmeg , Osmanthus , Parsley leaf , Pepper , Pepper black pepper , Pepper tree berry , Pine needle , Pizza , Pumpkin pie , Reseda , Root beer , Rose dog rose , Rose moss rose , Saffron , Sassafras , Snake root , Spice , Spicewood , Spikenard oil replacer , Tansy oil replacer , Tarragon oil replacer , Tolu balsam , Wormwood oil replacer
Flavoring purposes Angelica , Caraway seed , Carrot seed , Copaiba balsam , Coriander , Croton eluteria bark , Currant bud absolute replacer , Curry leaf , Dill weed , Galangal root , Guaiacwood , Marjoram , Mustard , Parsley leaf , Pepper black pepper , Pepper tabasco pepper , Pepper tree berry , Pine needle , Sarsaparilla , Snake root , Tansy oil replacer , Tarragon oil replacer , Tea black tea , Wasabi , Worcestershire sauce
Other purposes Boldus oil replacer , Pepper chili pepper , Watercress nasturtium

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for trans-carveol usage levels up to:
4.0000 % in the fragrance concentrate.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1197-07-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :443178
National Institute of Allergy and Infectious Diseases:Data
(1R,5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
Chemidplus:0002102581