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6485-40-1

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6485-40-1 Usage

Description

L-(-)-Carvone is the principal odor component of spearmint. It is with a refreshingly cool, minty odor and taste. It is used as flavor ingredient in a variety of foods and beverages, as well as in toothpaste and mouthwash. It is used as a fragrance in personal care products. It is intended for use in the manufacture of an area repellent for mosquitoes and biting flies. L-(-)-carvone is also used in agriculture as a sprout inhibitor of potatoes.

References

[1] Charles S Sell, The Chemistry of Fragrances: From Perfumer to Consumer, 2nd Edition, 2006 [2] https://www.epa.gov [3] K. J. Hartmans, P. Diepenhorst, W. Bakker and L. G. M. Gorris, The use of carvone in agriculture: sprout suppression of potatoes and antifungal activity against potato tuber and other plant diseases, Industrial Crops and Products, 1995, vol. 4, 3-13

Chemical Properties

Different sources of media describe the Chemical Properties of 6485-40-1 differently. You can refer to the following data:
1. clear colorless to pale yellow liquid
2. Caravone occurs in different forms. l-Carvone exhibits odor of spearmint, while d-carvone exhibits odor reminiscent of caraway.

Occurrence

R-Carvone is the main substance in spearmint oil, also present in toothpastes; it is the cause of delayed-type allergy resulting in cheilitis, but Hansson et al. also described a case of angioedema of the lips appearing within minutes after contact with toothpaste, with an open test resulting in an immediate and strong reaction to carvone.

Uses

(R)-(-)-Carvone is used in the flavor and food industry such as chewing gum additives. It is used in air freshening products such as in essential oils as well as in aromatherapy and alternative medicine. It is used to prepare carvomenthol, carvomenthone, dihydrocarvone, carveol and limonene. It reacts with lithium dimethylcuprate to place a methyl group trans to the isopropenyl group with good stereoselectivity. It is also used as a mosquito repellent and prevent premature sprouting of potatoes. Further, it is employed as an important starting material for the synthesis of enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1 and (4S,6R,7R)-trihydroxy-1-octyne derivatives. It is utilized as a vital raw material for the asymmetric total synthesis of natural products. In addition to this, it is used as a chiral starting material.

Definition

ChEBI: A carvone having (R) configuration.

Aroma threshold values

Detection: d-Carvone: 6.7 to 820 ppb; l-carvone: 2.7 to 600 ppb

General Description

(-)-Carvone, a monoterpene ketone which is the main active component of mentha plant species like Mentha spicata. It has antinociceptive activity which is found to be associated with decreased peripheral nerve excitability.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Carvone occurs in the dextro, levo and racemic form; l-carvone can be isolated from the essential oil of spearmint or is commercially synthesized from d-limonene; d-carvone is usually prepared by fractional distillation of oil of caraway, also from dillseed and dillweed oils, but this type differs in odor and flavors.

Check Digit Verification of cas no

The CAS Registry Mumber 6485-40-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,4,8 and 5 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 6485-40:
(6*6)+(5*4)+(4*8)+(3*5)+(2*4)+(1*0)=111
111 % 10 = 1
So 6485-40-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O2/c1-6(2)7-3-4-8(10)9(11)5-7/h4,7,10H,1,3,5H2,2H3/t7-/m1/s1

6485-40-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0703)  (R)-(-)-Carvone  >99.0%(GC)

  • 6485-40-1

  • 25mL

  • 175.00CNY

  • Detail
  • TCI America

  • (C0703)  (R)-(-)-Carvone  >99.0%(GC)

  • 6485-40-1

  • 100mL

  • 390.00CNY

  • Detail
  • TCI America

  • (C0703)  (R)-(-)-Carvone  >99.0%(GC)

  • 6485-40-1

  • 500mL

  • 1,240.00CNY

  • Detail
  • Alfa Aesar

  • (A13900)  (R)-(-)-Carvone, 98%   

  • 6485-40-1

  • 50g

  • 250.0CNY

  • Detail
  • Alfa Aesar

  • (A13900)  (R)-(-)-Carvone, 98%   

  • 6485-40-1

  • 250g

  • 1012.0CNY

  • Detail
  • Alfa Aesar

  • (A13900)  (R)-(-)-Carvone, 98%   

  • 6485-40-1

  • 1000g

  • 2020.0CNY

  • Detail
  • Sigma-Aldrich

  • (22060)  (−)-Carvone  analytical standard

  • 6485-40-1

  • 22060-1ML-F

  • 279.63CNY

  • Detail
  • Sigma-Aldrich

  • (22060)  (−)-Carvone  analytical standard

  • 6485-40-1

  • 22060-5ML-F

  • 404.82CNY

  • Detail
  • Sigma-Aldrich

  • (00290595)  (−)-Carvone  primary pharmaceutical reference standard

  • 6485-40-1

  • 00290595-100MG

  • 3,481.92CNY

  • Detail
  • Aldrich

  • (124931)  (R)-(−)-Carvone  98%

  • 6485-40-1

  • 124931-5ML

  • 387.27CNY

  • Detail
  • Aldrich

  • (124931)  (R)-(−)-Carvone  98%

  • 6485-40-1

  • 124931-100ML

  • 617.76CNY

  • Detail
  • Aldrich

  • (124931)  (R)-(−)-Carvone  98%

  • 6485-40-1

  • 124931-500ML

  • 1,838.07CNY

  • Detail

6485-40-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (-)-carvone

1.2 Other means of identification

Product number -
Other names (5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6485-40-1 SDS

6485-40-1Synthetic route

(+)-carvone
6485-40-1

(+)-carvone

2-methyl-5-(1-methyl-1-oxiranyl)-2-cyclohexen-1-one
56423-45-1

2-methyl-5-(1-methyl-1-oxiranyl)-2-cyclohexen-1-one

Conditions
ConditionsYield
With potassium superoxide; 2,4-dinitrobenzenesulfonyl chloride In acetonitrile at -35℃; for 4h;83%
With potassium superoxide; 2,4-dinitrobenzenesulfonyl chloride In acetonitrile at -35℃; for 4h; Product distribution; var. oxidation agent;83%
With Perbenzoic acid In chloroform at 20℃; for 14h;
(+)-carvone
6485-40-1

(+)-carvone

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

8-Hydroxycarvotanaceton-dinitrophenylhydrazon
43231-17-0, 81679-69-8

8-Hydroxycarvotanaceton-dinitrophenylhydrazon

Conditions
ConditionsYield
With sulfuric acid; water 1.) from -10 deg C to 0 deg C, 70 h, 2.) H2O, C2H5OH; Yield given. Multistep reaction;
(+)-carvone
6485-40-1

(+)-carvone

8,9-Dihydroxycarvotanaceton-dinitrophenylhydrazon
81679-68-7

8,9-Dihydroxycarvotanaceton-dinitrophenylhydrazon

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: perbenzoic acid / CHCl3 / 14 h / 20 °C
2: H2O, H2SO4 / CHCl3; ethanol
View Scheme

6485-40-1Relevant articles and documents

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

Athawale, Paresh R.,Zade, Vishal M.,Rama Krishna, Gamidi,Reddy, D. Srinivasa

supporting information, p. 6642 - 6647 (2021/09/02)

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold

Fiorio, Jhonatan L.,Rossi, Liane M.

, p. 312 - 318 (2021/01/29)

The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is

Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization

Zhang, Wuyuan,Fueyo, Elena Fernandez,Hollmann, Frank,Martin, Laura Leemans,Pesic, Milja,Wardenga, Rainer,H?hne, Matthias,Schmidt, Sandy

supporting information, p. 80 - 84 (2019/01/04)

In this study, we combined photo-organo redox catalysis and biocatalysis to achieve asymmetric C–H bond functionalization of simple alkane starting materials. The photo-organo catalyst anthraquinone sulfate (SAS) was employed to oxyfunctionalise alkanes to aldehydes and ketones. We coupled this light-driven reaction with asymmetric enzymatic functionalisations to yield chiral hydroxynitriles, amines, acyloins and α-chiral ketones with up to 99 % ee. In addition, we demonstrate functional group interconversion to alcohols, esters and carboxylic acids. The transformations can be performed as concurrent tandem reactions. We identified the degradation of substrates and inhibition of the biocatalysts as limiting factors affecting compatibility, due to reactive oxygen species generated in the photocatalytic step. These incompatibilities were addressed by reaction engineering, such as applying a two-phase system or temporal and spatial separation of the catalysts. Using a selection of eleven starting alkanes, one photo-organo catalyst and 8 diverse biocatalysts, we synthesized 26 products and report for the model compounds benzoin and mandelonitrile > 97 % ee at gram scale.

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