2D Structure

3D Structure

Carveol


Properties
PID PID00134
Mol. Weight 152.237 g/mol
LogP 3.12
Water solubility 0.0186 mol/L at 20 °C
Hydrogen Bond Donor 1
Hydrogen Bond Acceptor 1
Rotatable Bonds 1
XLogP3-AA 2.1

Carveol

Identifiers
Formula C10H16O
PubChem CID 7438
FEMA 2247
Flavor Profile Caraway, Fat, Fresh, Spearmint
Smiles C=C(C)C1CC=C(C)C(O)C1
InChl Key BAVONGHXFVOKBV-UHFFFAOYSA-N
InChl InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3
CAS Registry Number 99-48-9
IUPAC Systematic Name 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol

Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets


Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
Villous Amomum Equivalent plant: Amomum xanthioideSha Ren (砂仁)Amomi FructusWarm, PungentLung, Spleen, StomachView Graph

Pharmacological action

It has been found to exhibit chemoprevention of mammary carcinogenesis (prevents breast cancer).carveol is important compounds for food and cosmetics

industry.

Carveol is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic

products such as household cleaners and detergents. Its use worldwide is in the region of 0.1–1 metric tonnes per annum (IFRA, 2004).

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.



Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.

References

1. https://en.wikipedia.org/wiki/Carveol

2. Bhatia, S. P., McGinty, D., Letizia, C. S., Api, A. M. Fragrance material review on carveol[J]. Food and Chemical Toxicology, 2008, 46(11): S85-S87.

3. Hernandez-Ortega A, Vinaixa M, Zebec Z, et al. A toolbox for diverse oxyfunctionalisation of monoterpenes[J]. Scientific reports, 2018, 8.

4. Tecelão C S R, van Keulen F, da Fonseca M M R. Development of a reaction system for the selective conversion of (−)-trans-carveol to (−)-carvone with whole cells of Rhodococcus erythropolis DCL14[J]. Journal of Molecular Catalysis B: Enzymatic, 2001, 11(4-6): 719-724.

5. Młodzik, J., Wróblewska, A., Makuch, E., Wróbel, R. J., Michalkiewicz, B.. Fe/EuroPh catalysts for limonene oxidation to 1, 2-epoxylimonene, its diol, carveol, carvone and perillyl alcohol[J]. Catalysis Today, 2016, 268: 111-120.

6. Młodzik, J., Wróblewska, A., Makuch, E., Wróbel, R. J., Michalkiewicz, B. Fe/EuroPh catalysts for limonene oxidation to 1, 2-epoxylimonene, its diol, carveol, carvone and perillyl alcohol[J]. Catalysis Today, 2016, 268: 111-120.

7. Bouwmeester, H. J., Konings, M. C., Gershenzon, J., Karp, F., Croteau, R. Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum carvi)[J]. Phytochemistry, 1999, 50(2): 243-248.

8. Park, J. H., Jeon, Y. J., Lee, C. H., Chung, N., Lee, H. S. Insecticidal toxicities of carvacrol and thymol derived from Thymus vulgaris Lin. against Pochazia shantungensis Chou & Lu., newly recorded pest[J]. Scientific reports, 2017, 7: 40902.

9. De Carvalho C C C R, Da Fonseca M M R. Maintenance of cell viability in the biotransformation of (−)-carveol with whole cells of Rhodococcus erythropolis[J]. Journal of Molecular Catalysis B: Enzymatic, 2002, 19: 389-398.

10. Tak J H, Isman M B. Penetration-enhancement underlies synergy of plant essential oil terpenoids as insecticides in the cabbage looper, Trichoplusia ni[J]. Scientific reports, 2017, 7: 42432.

11. Khan A G, Sarangi M, Bhalla U S. Rats track odour trails accurately using a multi-layered strategy with near-optimal sampling[J]. Nature communications, 2012, 3: 703.