Carvone

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540062

CAS#: 99-49-0

Description: Carvone is a TRPV3 agonist found in spearmint oil used commercially as a food additive and fragrance. It is known to suppress cell proliferation in prostate cancer cells and inhibits growth of Dermatophagoides.


Chemical Structure

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Carvone
CAS# 99-49-0

Theoretical Analysis

MedKoo Cat#: 540062
Name: Carvone
CAS#: 99-49-0
Chemical Formula: C10H16O
Exact Mass: 152.1201
Molecular Weight: 152.23
Elemental Analysis: C, 78.90; H, 10.59; O, 10.51

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Related CAS #: 99-49-0   2244-16-8 (D-)   6485-40-1 (L-)  

Synonym: Carvone, Carveol; L-Carveol; BRN 1861032; BRN-1861032; BRN1861032; AI3 27596; AI3-27596; AI327596; NSC 68313; NSC-68313; NSC68313

IUPAC/Chemical Name: 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol

InChi Key: BAVONGHXFVOKBV-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3

SMILES Code: OC1C(C)=CCC(C(C)=C)C1

Appearance: Off-white to light yellow solid powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 152.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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3: Morrish JL, Daugulis AJ. Improved reactor performance and operability in the biotransformation of carveol to carvone using a solid-liquid two-phase partitioning bioreactor. Biotechnol Bioeng. 2008 Dec 1;101(5):946-56. doi: 10.1002/bit.21957. PubMed PMID: 18546419.

4: Bhatia SP, McGinty D, Letizia CS, Api AM. Fragrance material review on carveol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S85-7. doi: 10.1016/j.fct.2008.06.032. Epub 2008 Jul 1. Review. PubMed PMID: 18640224.

5: Ringer KL, Davis EM, Croteau R. Monoterpene metabolism. Cloning, expression, and characterization of (-)-isopiperitenol/(-)-carveol dehydrogenase of peppermint and spearmint. Plant Physiol. 2005 Mar;137(3):863-72. Epub 2005 Feb 25. PubMed PMID: 15734920; PubMed Central PMCID: PMC1065387.

6: van der Werf MJ, Boot AM. Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14. Microbiology. 2000 May;146 ( Pt 5):1129-41. PubMed PMID: 10832640.

7: Duetz WA, Fjällman AH, Ren S, Jourdat C, Witholt B. Biotransformation of D-limonene to (+) trans-carveol by toluene-grown Rhodococcus opacus PWD4 cells. Appl Environ Microbiol. 2001 Jun;67(6):2829-32. PubMed PMID: 11375201; PubMed Central PMCID: PMC92945.

8: van der Werf MJ, van der Ven C, Barbirato F, Eppink MH, de Bont JA, van Berkel WJ. Stereoselective carveol dehydrogenase from Rhodococcus erythropolis DCL14. A novel nicotinoprotein belonging to the short chain dehydrogenase/reductase superfamily. J Biol Chem. 1999 Sep 10;274(37):26296-304. PubMed PMID: 10473585.

9: Miyazawa M, Shindo M, Shimada T. Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes. Chem Res Toxicol. 2002 Jan;15(1):15-20. PubMed PMID: 11800592.

10: Li Lin A, Shangari N, Chan TS, Remirez D, O'Brien PJ. Herbal monoterpene alcohols inhibit propofol metabolism and prolong anesthesia time. Life Sci. 2006 May 30;79(1):21-9. Epub 2006 Jan 24. PubMed PMID: 16436284.

11: Moon H, Kim MJ, Son HJ, Kweon HJ, Kim JT, Kim Y, Shim J, Suh BC, Rhyu MR. Five hTRPA1 Agonists Found in Indigenous Korean Mint, Agastache rugosa. PLoS One. 2015 May 15;10(5):e0127060. doi: 10.1371/journal.pone.0127060. eCollection 2015. PubMed PMID: 25978436; PubMed Central PMCID: PMC4433173.

12: Morrish JL, Daugulis AJ. Inhibitory effects of substrate and product on the carvone biotransformation activity of Rhodococcus erythropolis. Biotechnol Lett. 2008 Jul;30(7):1245-50. doi: 10.1007/s10529-008-9686-5. Epub 2008 Mar 8. Erratum in: Biotechnol Lett. 2008 Jul;30(7):1251. PubMed PMID: 18327538.

13: Shimada T, Shindo M, Miyazawa M. Species differences in the metabolism of (+)- and (-)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, rabbits, dogs, monkeys, and humans. Drug Metab Pharmacokinet. 2002;17(6):507-15. PubMed PMID: 15618705.

14: Wang M, Xi H, Cun D, Chen Y, Xu Y, Fang L. l-Carvyl esters as penetration enhancers for the transdermal delivery of 5-fluorouracil. AAPS PharmSciTech. 2013 Jun;14(2):669-74. doi: 10.1208/s12249-013-9952-2. Epub 2013 Mar 30. PubMed PMID: 23543605; PubMed Central PMCID: PMC3665999.

15: Morrish JL, Brennan ET, Dry HC, Daugulis AJ. Enhanced bioproduction of carvone in a two-liquid-phase partitioning bioreactor with a highly hydrophobic biocatalyst. Biotechnol Bioeng. 2008 Nov 1;101(4):768-75. doi: 10.1002/bit.21941. PubMed PMID: 18478563.

16: Govindarajan M, Sivakumar R, Rajeswari M, Yogalakshmi K. Chemical composition and larvicidal activity of essential oil from Mentha spicata (Linn.) against three mosquito species. Parasitol Res. 2012 May;110(5):2023-32. doi: 10.1007/s00436-011-2731-7. Epub 2011 Dec 6. PubMed PMID: 22139403.

17: Schmidt L, Göen T. R-Limonene metabolism in humans and metabolite kinetics after oral administration. Arch Toxicol. 2017 Mar;91(3):1175-1185. doi: 10.1007/s00204-016-1751-6. Epub 2016 Jun 21. PubMed PMID: 27325307.

18: Wróblewska A. The epoxidation of limonene over the TS-1 and Ti-SBA-15 catalysts. Molecules. 2014 Nov 28;19(12):19907-22. doi: 10.3390/molecules191219907. PubMed PMID: 25460313.

19: Gonçalves JC, Alves Ade M, de Araújo AE, Cruz JS, Araújo DA. Distinct effects of carvone analogues on the isolated nerve of rats. Eur J Pharmacol. 2010 Oct 25;645(1-3):108-12. doi: 10.1016/j.ejphar.2010.07.027. Epub 2010 Jul 27. PubMed PMID: 20670618.

20: Kawasaki H, Mizuta K, Fujita T, Kumamoto E. Inhibition by menthol and its related chemicals of compound action potentials in frog sciatic nerves. Life Sci. 2013 Mar 14;92(6-7):359-67. doi: 10.1016/j.lfs.2013.01.012. Epub 2013 Jan 24. PubMed PMID: 23352972.