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cis-carveol

cis-carveol is a naturally occurring monoterpenoid alcohol used for flavor and fragrance applications, noted for its spicy odor and presence in various essential oils.
Chemical Structure

General Material Description

cis-Carveol, also known as (Z)-carveol or cis-p-mentha-1,8-dien-6-ol, is a monoterpenoid alcohol characterized by the molecular formula C10H16O. It typically occurs as a mixture with undefined chiral purity, possessing a cis stereochemical arrangement relative to the isopropenyl group. The compound features a spicy odor reminiscent of caraway, contributing to its utility in flavor and fragrance formulations. cis-Carveol is a naturally occurring ingredient found as a minor constituent in numerous essential oils derived from plant sources such as caraway seed, blood orange, and various herbal oils. More information can be accessed through the ChEBI database. It is primarily obtained by extraction from natural essential oils or synthesized for use in aroma compositions.

cis-carveol with 6S* as stereochemical center, cis relative to isopropenyl group, in practice it is a mixture or undefined chiral purity.

Occurrence, Applicability & Potential Uses

cis-Carveol naturally occurs in a variety of essential oils including those from caraway seed, blood orange, spearmint, and eucalyptus species. It is present in concentrations ranging from trace levels to approximately 0.5% in these oils, depending on the botanical source. Its spicy, caraway-like aroma makes it valuable as a flavor additive and fragrance agent. The compound is employed to impart warm, spicy notes in perfumery and flavor formulations, covering applications from food flavorings to personal care product scents. Use guidelines for cis-carveol conform to the International Fragrance Association's (IFRA) Code of Practice (Global), with recommended maximum concentrations around 4% in fragrance concentrates. This regulatory framework ensures appropriate use levels to maintain consumer safety and product performance.

Physico-Chemical Properties Summary

cis-Carveol exhibits physicochemical properties that influence its behavior in formulations. It has a molecular weight of approximately 152.24 g/mol and shows moderate lipophilicity, with an estimated logP around 2.8 indicating solubility in organic solvents and limited water miscibility. The compound's vapor pressure is low, at 0.012 mmHg at 25 °C, reflecting relatively low volatility under ambient conditions. Its flash point, measured by the tagged-cup method, is 196 °F (approximately 91 °C), suggesting stability during common formulation processes. cis-Carveol is soluble in alcohol and has limited solubility in water, which affects its incorporation in aqueous systems. These properties must be considered in fragrance and flavor creation to optimize intensity, stability, and delivery of its characteristic spicy aroma.

FAQ

What is cis-carveol and what are its sensory characteristics?
cis-Carveol is a monoterpenoid alcohol identified by the chemical formula C10H16O, known for its presence in various essential oils such as caraway seed and blood orange. It exhibits a spicy odor reminiscent of caraway and serves as an important flavor and fragrance component. The compound's structure includes a cis configuration relative to its isopropenyl group, contributing to its distinct scent profile.
Where is cis-carveol commonly found and how is it used?
This compound occurs naturally in essential oils from plants including caraway, blood orange, spearmint, and eucalyptus species at varying trace concentrations. cis-Carveol is utilized primarily in flavor and fragrance applications to impart spicy and warm notes. It is incorporated in formulations for products such as perfumes, colognes, and flavor blends in the food industry.
What regulatory standards apply to cis-carveol and how is it sourced?
Sourcing of cis-carveol typically involves extraction from natural essential oils or chemical synthesis. It is regulated under the International Fragrance Association's (IFRA) global Code of Practice, which recommends usage limits to ensure safety—commonly up to 4% concentration in fragrance concentrates. No significant hazard classification applies under OSHA standards, reflecting its general compliance for flavor and fragrance use.

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

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Literature & References

Leffingwell:Chirality or Article
(1R,5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):330573
Pubchem (sid):10505349
Flavornet:1197-06-4
Pherobase:View
Publications by PubMed
GC-MS characterisation and antibacterial activity evaluation of Nigella sativa oil against diverse strains of Salmonella.
Chemical composition, cytotoxicity and in vitro antitrypanosomal and antiplasmodial activity of the essential oils of four Cymbopogon species from Benin.
Chemical composition and insecticidal activity of the essential oil of Illicium pachyphyllum fruits against two grain storage insects.
Chemical composition and larvicidal activity of essential oil from Mentha spicata (Linn.) against three mosquito species.
Insecticidal activity of essential oil of Carum Carvi fruits from China and its main components against two grain storage insects.
Enhanced bioproduction of carvone in a two-liquid-phase partitioning bioreactor with a highly hydrophobic biocatalyst.
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.
Repellency of essential oils of some Kenyan plants against Anopheles gambiae.
Changes of the volatile profile and artifact formation in Daidai (Citrus aurantium) cold-pressed peel oil on storage.
Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation.
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.

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
UM BBD:Search
KEGG (GenomeNet):C11395
HMDB (The Human Metabolome Database):Search
FooDB:FDB003843
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

General Material Information

Preferred name cis-carveol
Trivial Name (Z)-carveol
Short Description cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol
Formula C10 H16 O
CAS Number 1197-06-4
FDA UNII OOZ105PLI9
Nikkaji Number J9.138C
xLogP3-AA 2.10 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • (±)-cis-carveol
  • (1R,5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
  • (Z)-carveol
  • 2-cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R,5R)-rel-
  • 2-cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, cis-
  • cis-2-methyl-5-(1-methyl ethenyl)-2-cyclohexen-1-ol
  • cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol
  • cis-2-Methyl-5-(1-methylvinyl)-2-cyclohexene-1-ol
  • cis-Mentha-1,8-dien-6-ol
  • cis-p-mentha-1,8-dien-6-ol
  • cis-para-mentha-1,8-dien-6-ol
  • NSC 319644
  • p-mentha-6,8-dien-2-ol
  • p-mentha-6,8-dien-2-ol, cis-
  • rel-(1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Vapor Pressure 0.012 mmHg @ 25 °C
Flash Point TCC Value 91.2 °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, spicy
General comment At 100.00 %. caraway

Occurrences

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 cis-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 ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :330573
National Institute of Allergy and Infectious Diseases:Data
(1R,5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
Chemidplus:0001197064