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Carvone

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8 API Suppliers, 4 USDMF, 2 CEP/COS, 2 EU WC, $ API Reference Price

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4 USDMF
2 CEP/COS
2 EU WC
$ API Reference Price

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2 FDF Dossiers, 2 Europe

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2 Europe

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4 APIs, 2 EXCIPIENTS

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2 EXCIPIENTS

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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 99-49-0, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone, Karvon, Dl-carvone, 1-carvone, P-mentha-6,8-dien-2-one

Molecular Formula

C₁₀H₁₄O

Molecular Weight

150.22 g/mol

InChI Key

ULDHMXUKGWMISQ-UHFFFAOYSA-N

FDA UNII

75GK9XIA8I

Carvone is a metabolite found in or produced by Saccharomyces cerevisiae.

1 2D Structure

Carvone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one

2.1.2 InChI

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3

2.1.3 InChI Key

ULDHMXUKGWMISQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CCC(CC1=O)C(=C)C

2.2 Other Identifiers

2.2.1 UNII

75GK9XIA8I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (rs)-5-isopropenyl-2-methylcyclohex-2-en-1-one

2. 2-methyl-5-(1-methylethenyl)-2-cyclohexene-1-one

3. 2-methyl-5-isopropenyl-2-cyclohexenone

4. 5-isopropyl-2-methyl-2-cyclohexen-1-one

5. Carvone, (+--)-

6. Carvone, (r)-isomer

7. Carvone, (s)-isomer

8. Limonen-6-one

2.3.2 Depositor-Supplied Synonyms

1. 99-49-0

2. 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

3. Karvon

4. Dl-carvone

5. 1-carvone

6. P-mentha-6,8-dien-2-one

7. 2-methyl-5-isopropenyl-2-cyclohexenone

8. Carvone [iso]

9. D-cavone

10. 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one

11. 2-cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-

12. 6,8(9)-p-menthadien-2-one

13. 2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one

14. Nci-c55867

15. (+/-)-carvone

16. 6,8-p-menthadien-2-one

17. 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one

18. 75gk9xia8i

19. P-mentha-6,8-dien-2-one, (r)-(-)-

20. 2-cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (r)-

21. Chebi:38265

22. P-mentha-1(6),8-dien-2-one

23. Nsc6275

24. Nsc-6275

25. 2-methyl-5-(1-methylethenyl)-2-cyclohexene-1-one

26. Mfcd00062996

27. Carvone 100 Microg/ml In Acetonitrile

28. Carvone (natural)

29. L-6,8(9)-p-menthadien-2-one

30. Fema Number 2249

31. 6,8-p-menthadien-2-on

32. Limonen-6-one

33. D-p-mentha-1(6),8-dien-2-one

34. Fema No. 2249

35. Hsdb 707

36. (+-)-carvone

37. Nsc 6275

38. Einecs 202-759-5

39. Unii-75gk9xia8i

40. Delta(sup 6,8)-(9)-terpadienone-2

41. Brn 1364206

42. Carvon

43. A Carvone

44. Ai3-08877

45. Mfcd00001578

46. Mfcd00062997

47. D-p-mentha-6,8,(9)-dien-2-one

48. .alpha.-carvone

49. Delta-1-methyl-4-isopropenyl-6-cyclohexen-2-one

50. 5-isopropenyl-2-methylcyclohex-2-en-1-one

51. Carvone [hsdb]

52. Carvone [inci]

53. Carvone [mi]

54. Carvone, Dl-

55. 5-isopropenyl-2-methyl-cyclohex-2-en-1-one

56. 2-methyl-5-(1-propen-2-yl)-2-cyclohexenone

57. Dsstox_cid_27426

58. Dsstox_rid_82339

59. Nciopen2_001348

60. (rs)-5-isopropenyl-2-methylcyclohex-2-en-1-one

61. Dsstox_gsid_47426

62. Schembl39408

63. 4-07-00-00316 (beilstein Handbook Reference)

64. Carvone Dl-form [mi]

65. Chembl15676

66. Carvone, (+-)-

67. Carvone, (+/-)-

68. Dtxsid8047426

69. Amy4152

70. Hms1789n08

71. Nsc93738

72. Tox21_302547

73. Bbl010103

74. Nsc-93738

75. Stk801456

76. Akos000121377

77. Akos016843655

78. Cas-99-49-0

79. Ncgc00256915-01

80. Wln: L6v Butj B1 Ey1 & U1

81. .delta.(sup 6,8)-(9)-terpadienone-2

82. As-10471

83. Nci60_008753

84. Sy010704

85. Sy012922

86. Sy274718

87. 2-methyl-5-isopropenyl-2-cyclohexen-1-one

88. Db-054736

89. Cs-0033814

90. Ft-0600385

91. Ft-0605067

92. Ft-0658046

93. Fema No. 2249, (+/-)-

94. O10834

95. (-)-2-methyl-5-isopropenyl-2-cyclohexen-1-one

96. A858458

97. Q416800

98. .delta.-1-methyl-4-isopropenyl-6-cyclohexen-2-one

99. 5-isopropenyl-2-methyl-2-cyclohexen-1-one, (r)-

100. W-100036

101. 2-methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-one

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₄O
Molecular Weight	150.22 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	150.104465066 g/mol
Monoisotopic Mass	150.104465066 g/mol
Topological Polar Surface Area	17.1 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	223
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Veterinary use: Carvi aetheroleum (containing D-carvone) is used in veterinary medicinal products to facilitate breathing in new-borne animals, and to treat flatulence and disturbances of the stomach and the gut in farmed animals.

EFSA Journal 12 (7): 3806 (2014)

...Carvi aetheroleum and carvi fructus are registered as herbal medicinal products by the European Medicines Agency. Uses as a laxative, in colic treatment, as a breath freshener, or to help digestion in young children have been reported. Other properties claimed for caraway seeds include antispasmodic, carminative, emmenagogue, expectorant, galactagogue, stimulant, stomachic, and tonic properties.

EFSA Journal 12 (7): 3806 (2014)

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

5.2 Absorption, Distribution and Excretion

In humans, D-carvone pharmacokinetics was investigated in 15 male volunteers who, after a 10 hr fast, took 5 capsules of an immediate release formulation containing 20 mg caraway oil. Carvone concentrations in plasma were determined by GC/MS, with a limit of quantification of 0.5 ng/mL for carvone. Pharmacokinetic parameters were determined, i.e., area-under the plasma-concentration curve (AUC) of 28.9+/- 20.0 ng.mL/hr , plasma peak concentration (Cmax) of 14.8+/-10.4 ng/mL with a time to reach Cmax (Tmax) of 1.3 hours and a half life of 2.4 hours. Inter-individual differences determined as the coefficients of variation in AUC, Cmax, and t1/2 were 69%, 74%, and 50% respectively. /D-Carvone/

EFSA Journal 12 (7): 3806 (2014)

5.3 Metabolism/Metabolites

As part of a program aiming at the selection of yeast strains which might be of interest as sources of natural flavors and fragrances, the bioreduction of (4R)-(-)-carvone and (1R)-(-)-myrtenal by whole-cells of non-conventional yeasts (NCYs) belonging to the genera Candida, Cryptococcus, Debaryomyces, Hanseniaspora, Kazachstania, Kluyveromyces, Lindnera, Nakaseomyces, Vanderwaltozyma, and Wickerhamomyces was studied. Volatiles produced were sampled by means of headspace solid-phase microextraction (SPME) and the compounds were analyzed and identified by gas chromatography-mass spectroscopy (GC-MS). Yields (expressed as % of biotransformation) varied in dependence of the strain. The reduction of both (4R)-(-)-carvone and (1R)-(-)-myrtenal were catalyzed by some ene-reductases (ERs) and/or carbonyl reductases (CRs), which determined the formation of (1R,4R)-dihydrocarvone and (1R)-myrtenol respectively, as main flavoring products. The potential of NCYs as novel whole-cell biocatalysts for selective biotransformation of electron-poor alkenes for producing flavors and fragrances of industrial interest is discussed.

PMID:23681058 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270020 Goretti M et al; Molecules 18 (5): 5736-48 (2013)

... Ketones (e.g., carvone and menthone) are reduced to secondary alcohols which are then excreted as glucuronides.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 149

The cyclic monoterpene ketone (-)-carvone was metabolized by the plant pathogenic fungus Absidia glauca. After 4 days of incubation, the diol 10-hydroxy-(+)-neodihydrocarveol was formed. The absolute configuration and structure of the crystalline substance was identified by means of X-ray diffraction and by spectroscopic techniques (MS, IR, and NMR). The antimicrobial activity of the substrate and metabolite was assayed with human pathogenic microorganisms.

PMID:18998407 Demirci F et al; Z Naturforsch C 59 (5-6): 389-92 (2004)

D-Carvone toxicokinetics in humans features rapid elimination with a half life of 2.4 hours, no data are available for L-carvone. No toxicokinetic data on carvone in animals are available. The evidence from in vivo, in vitro, and in silico assessments has shown that carvone metabolism is likely to be different in humans and rats - with further possible differences between metabolism in male and female rats. It is also evident that when compared with carvone itself, the metabolites are not likely to be different in terms of GI uptake or half-life in the body. Toxicokinetic data on other monoterpenes in the rat such as menthol suggest that metabolism involves conjugation to a glucuronide for which enterohepatic recirculation occurs in the rat but not in humans. Considering the molecular weight of glucuronidated carvone metabolites, they may undergo enterohepatic recirculation in rats but not in humans, making the rat more sensitive than humans for these compounds. /D-Carvone and L-Carvone/

EFSA Journal 12 (7): 3806 (2014)

In vivo metabolism of D- and L-carvone has been investigated in six human volunteers (three males, three females) after oral dosing (1 mg/kg bw), with collection of urine samples 24 hr before and after the ingestion of each enantiomer separately. Chemical structures of the metabolites were elucidated using mass spectral analysis in combination with metabolite syntheses and NMR analysis. For this, the urinary samples were treated with sulphatase and glucuronidase, assuming conjugation of phase I metabolites. However, no quantitative data on excretion of conjugated forms of the metabolites were reported. The study identified three side-chain oxidation products as the main primary unconjugated metabolites of D- and L-carvone: dihydrocarvonic acid, carvonic acid, and uroterpenolone, with 10-hydroxycarvone as the proposed intermediate metabolic step. However, unlike other species, the presence of 10-hydroxycarvone was not detected in humans and /it was/ suggested this was due to more efficient oxidation of 10-hydroxycarvone leading to carvonic acid. According to /the study/, there were no differences in the metabolism of D- and L-carvone. However, the results presented only refer to "after carvone ingestion", although apparently both carvone enantiomers were ingested by the volunteers in independent trials. According to the author, all metabolites were identical after the application of either D- or L-carvone. However, the configurations of metabolites were not identified and the chromatographic analyses were only performed on a nonchiral stationary phase. This experimental set-up does not allow differentiation of the stereospecific metabolism of D- and L-carvone. /D-Carvone and L-Carvone/

EFSA Journal 12 (7): 3806 (2014)

5.4 Biological Half-Life

D-Carvone toxicokinetics in humans features rapid elimination with a half life of 2.4 hours, no data are available for L-carvone. /D-Carvone/

EFSA Journal 12 (7): 3806 (2014)

API SUPPLIERS

01

Kerry

U.S.A

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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02

Symrise

Germany

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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03

Symrise

Germany

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Medlab Asia & Asia Health

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04

Fona International

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Medlab Asia & Asia Health

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Frey + Lau GmbH

Germany

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

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06

Frey + Lau GmbH

Germany

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

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07

Norex Flavours

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

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08

Bhagat Aromatics

India

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Medlab Asia & Asia Health

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API Reference Price

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