Carveol

Carveol
(1R,5R)-Carveol
((–)-cis)
(1S,5R)-Carveol
((–)-trans)
(1R,5S)-Carveol
((+)-trans)
(1S,5S)-Carveol
((+)-cis)
Names
Preferred IUPAC name
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Other names
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol
Mentha-6,8-dien-2-ol
Identifiers
CAS Number
  • 99-48-9 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
3DMet
  • B04334
Beilstein Reference
 1861032
ChEBI
  • CHEBI:23046 checkY
  • CHEBI:227
  • CHEBI:232
ChEMBL
  • ChEMBL1385229 ☒N
  • ChEMBL1907992
  • ChEMBL1908058
ChemSpider
  • 7160 ☒N
  • 2006207 (5R) checkY
  • 9259214 (5S) checkY
  • 292842 (1R,5R) checkY
  • 391450 (1R,5S) checkY
ECHA InfoCard 100.002.507 Edit this at Wikidata
EC Number
  • 202-757-4
IUPHAR/BPS
  • 6417
KEGG
  • C11395 ☒N
MeSH Carveol
PubChem CID
  • 7438
  • 2724032 (5R)
  • 11084068 (5S)
  • 330573 (1R,5R)
  • 443178 (1R,5S)
RTECS number
  • OS8400000
UNII
  • 1L9KXT85R9 checkY
CompTox Dashboard (EPA)
  • DTXSID3024736 Edit this at Wikidata
InChI
  • InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3 ☒N
    Key: BAVONGHXFVOKBV-UHFFFAOYSA-N ☒N
  • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3
  • CC(=C)C1CC=C(C)C(O)C1
  • OC1C(=C/CC(/C(=C)C)C1)\C
Properties
Chemical formula
 C10H16O
Molar mass 152.237 g·mol−1
Density 0.958 g cm−3
Boiling point 226 to 227 °C (439 to 441 °F; 499 to 500 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 98 °C (208 °F; 371 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Carveol is a natural unsaturated, monocyclic monoterpenoid alcohol that is a constituent of spearmint essential oil in the form of cis-(−)-carveol. It is a colorless fluid soluble in oils, but insoluble in water and has an odor and flavor that resemble those of spearmint and caraway. Consequently, it is used as a fragrance in cosmetics and as a flavor additive in the food industry.

It has been found to exhibit chemoprevention of mammary carcinogenesis (prevents breast cancer).[1]

An alpha-trans-dihydroxy derivative, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol, possesses potent antiparkinsonian activity in animal models.[2]

References

  1. ^ Crowell, PL; Kennan, WS; Haag, JD; Ahmad, S; Vedejs, E; Gould, MN (1992). "Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene". Carcinogenesis. 13 (7): 1261–4. doi:10.1093/carcin/13.7.1261. PMID 1638695.
  2. ^ Ardashov, Oleg V.; Pavlova, Alla V.; Il’Ina, Irina V.; Morozova, Ekaterina A.; Korchagina, Dina V.; Karpova, Elena V.; Volcho, Konstantin P.; Tolstikova, Tat’Yana G.; Salakhutdinov, Nariman F. (2011). "Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson's Disease". Journal of Medicinal Chemistry. 54 (11): 3866–3874. doi:10.1021/jm2001579. PMID 21534547.