{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460021204 | ImageFileL1 = 1R,5R-Carveol.png | ImageCaptionL1 = (1''R'',5''R'')-Carveol<br>((–)-''cis'') | ImageFileR1 = 1S,5R-Carveol.png | ImageCaptionR1 = (1''S'',5''R'')-Carveol<br>((–)-''trans'') | ImageFileL2 = 1R,5S-Carveol.png | ImageCaptionL2 = (1''R'',5''S'')-Carveol<br>((+)-''trans'') | ImageFileR2 = 1S,5S-Carveol.png | ImageCaptionR2 = (1''S'',5''S'')-Carveol<br>((+)-''cis'') | PIN = 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol | OtherNames = 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol<br />Mentha-6,8-dien-2-ol |Section1={{Chembox Identifiers | IUPHAR_ligand = 6417 | CASNo = 99-48-9 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 1L9KXT85R9 | PubChem = 7438 | PubChem1 = 2724032 | PubChem1_Comment = (5''R'') | PubChem2 = 11084068 | PubChem2_Comment = (5''S'') | PubChem3 = 330573 | PubChem3_Comment = (1''R'',5''R'') | PubChem4 = 443178 | PubChem4_Comment = (1''R'',5''S'') | ChemSpiderID = 7160 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID1 = 2006207 | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1_Comment = (5''R'') | ChemSpiderID2 = 9259214 | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID2_Comment = (5''S'') | ChemSpiderID3 = 292842 | ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID3_Comment = (1''R'',5''R'') | ChemSpiderID4 = 391450 | ChemSpiderID4_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID4_Comment = (1''R'',5''S'') | EINECS = 202-757-4 | KEGG = C11395 | KEGG_Ref = {{keggcite|changed|kegg}} | MeSHName = Carveol | ChEMBL = 1385229 | ChEMBL1 = 1907992 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL5 = 1908058 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 23046 | ChEBI1=227 | ChEBI2=232 | RTECS = OS8400000 | Beilstein = 1861032 | 3DMet = B04334 | SMILES = CC(=C)C1CC=C(C)C(O)C1 | SMILES1 = OC1C(=C/CC(/C(=C)C)C1)\C | StdInChI = 1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | InChI = 1/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3 | StdInChIKey = BAVONGHXFVOKBV-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} }} |Section2={{Chembox Properties | C=10 | H=16 | O=1 | Density = 0.958 g cm<sup>−3</sup> | BoilingPtC = 226 to 227 }} |Section3={{Chembox Hazards | GHSPictograms = {{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|315|319|335}} | PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} | NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0 | FlashPtC = 98 }} }}

'''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).<ref>{{cite journal | pmid = 1638695 | year = 1992 | last1 = Crowell | first1 = PL | last2 = Kennan | first2 = WS | last3 = Haag | first3 = JD | last4 = Ahmad | first4 = S | last5 = Vedejs | first5 = E | last6 = Gould | first6 = MN | title = Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene | volume = 13 | issue = 7 | pages = 1261–4 | journal = Carcinogenesis | doi=10.1093/carcin/13.7.1261}}</ref>

An ''alpha''-''trans''-dihydroxy derivative, (1''R'',2''R'',6''S'')-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol, possesses potent antiparkinsonian activity in animal models.<ref>{{cite journal | doi = 10.1021/jm2001579 | title = Highly Potent Activity of (1''R'',2''R'',6''S'')-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson's Disease | year = 2011 | last1 = Ardashov | first1 = Oleg V. | last2 = Pavlova | first2 = Alla V. | last3 = Il’Ina | first3 = Irina V. | last4 = Morozova | first4 = Ekaterina A. | last5 = Korchagina | first5 = Dina V. | last6 = Karpova | first6 = Elena V. | last7 = Volcho | first7 = Konstantin P. | last8 = Tolstikova | first8 = Tat’Yana G. | last9 = Salakhutdinov | first9 = Nariman F. | journal = Journal of Medicinal Chemistry | volume = 54 | issue = 11 | pages = 3866–3874 | pmid = 21534547 }}</ref>

==Biosynthesis== Monoterpenes such as carveol are produced from geranyl pyrophosphate.<ref>{{cite journal|title=Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes|author1=Davis, Edward M. |author2=Croteau, Rodney |journal=Topics in Current Chemistry|year=2000|volume=209|pages=53–95|doi=10.1007/3-540-48146-X_2|isbn=978-3-540-66573-1}}</ref> The immediate precursor in plants including peppermint and spearmint is limonene.<ref name=Karp>{{cite journal |vauthors=Karp F, Mihaliak CA, Harris JL, Croteau R | date = 1990 | title = Monoterpene biosynthesis: specificity of the hydroxylations of (−)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves | journal = Arch. Biochem. Biophys. | volume = 276 | pages = 219&ndash;26 | pmid = 2297225 | doi = 10.1016/0003-9861(90)90029-X | issue = 1 }}</ref> Oxidation of the (''S'') enantiomer by (S)-limonene 6-monooxygenase gives (−)-trans-carveol:

{{chemrxn|width=35%| {{chemrxn/cpd|qid=Q27089405|caption=(''S'')-limonene }} {{chemrxn/arw| }} {{chemrxn/cpd|qid=Q27089409|caption=(−)-trans-carveol }} }}

An alternative enzyme, (R)-limonene 6-monooxygenase is present in caraway and gives (+)-trans-carveol.<ref>{{cite journal | author = Croteau R | date = 1999 | title = Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum Carvi) | journal = Phytochemistry | volume = 50 | pages = 243&ndash;248 | doi = 10.1016/S0031-9422(98)00516-0 | issue = 2 }}</ref>

{{chemrxn|width=35%| {{chemrxn/cpd|qid=Q27888324|caption=(''R'')-limonene }} {{chemrxn/arw| }} {{chemrxn/cpd|qid=Q27089408|caption=(+)-trans-carveol }} }}

==References== {{Reflist}}

Category:Monoterpenes Category:Cyclohexenols