L(-)-Carvone CAS 6485-40-1
Introduction：Basic information about L(-)-Carvone CAS 6485-40-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
L(-)-Carvone Basic informationDescription References
| Product Name: | L(-)-Carvone |
| Synonyms: | (L)-(-)-P-MENTHA-6,8-DIEN-2-ONE;L-P-MENTHA-6,8-DIEN-2-ONE;LAEVO-CARVEONE;L(-)-CARVONE;L-CARVONE;L-1-METHYL-4-ISOPROPENYL-6-CYCLOHEXEN-2-ONE;FEMA 2249;CARVONE, (-)- |
| CAS: | 6485-40-1 |
| MF: | C10H14O |
| MW: | 150.22 |
| EINECS: | 229-352-5 |
| Product Categories: | Aromatic Ketones (substituted);Biochemistry;Monocyclic Monoterpenes;Terpenes |
| Mol File: | 6485-40-1.mol |
L(-)-Carvone Chemical Properties
| Melting point | 25°C |
| alpha | -57 º (neat) |
| Boiling point | 227-230 °C (lit.) |
| density | 0.959 g/mL at 25 °C (lit.) |
| vapor density | 5.2 (vs air) |
| vapor pressure | 0.4 mm Hg ( 20 °C) |
| refractive index | n |
| FEMA | 2249 | CARVONE |
| Fp | 192 °F |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| solubility | Chloroform, Methanol |
| form | Liquid |
| color | Clear colorless to pale yellow |
| Odor | at 100.00 %. sweet spearmint herbal minty |
| Odor Type | minty |
| Optical Rotation | [α]20/D 61°, neat |
| biological source | synthetic |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Merck | 14,1874 |
| JECFA Number | 380 |
| BRN | 2206714 |
| Dielectric constant | 11.0（22℃） |
| Major Application | flavors and fragrances |
| Cosmetics Ingredients Functions | PERFUMING FRAGRANCE FLAVOURING |
| InChI | 1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1 |
| InChIKey | ULDHMXUKGWMISQ-SECBINFHSA-N |
| SMILES | CC(=C)[C@@H]1CC=C(C)C(=O)C1 |
| LogP | 2.74 at 20-37℃ |
| CAS DataBase Reference | 6485-40-1(CAS DataBase Reference) |
| NIST Chemistry Reference | Carvone(6485-40-1) |
| EPA Substance Registry System | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)- (6485-40-1) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22 |
| Safety Statements | 36-24/25 |
| WGK Germany | 2 |
| RTECS | OS8650000 |
| F | 8-10-23 |
| TSCA | TSCA listed |
| HS Code | 29142900 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Acute Tox. 4 Oral Skin Sens. 1 |
| 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 | clear colorless to pale yellow liquid |
| Chemical Properties | Caravone occurs in different forms. l-Carvone exhibits odor of spearmint, while d-carvone exhibits odor reminiscentof 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 oris commercially synthesized from d-limonene; d-carvone is usually prepared by fractional distillation of oil of caraway, also fromdillseed and dillweed oils, but this type differs in odor and flavors. |
L(-)-Carvone Preparation Products And Raw materials
| Raw materials | Hydrogen Sulfide-->Sulfurous Acid-->(+)-Dipentene-->Spearmint oil |
| Preparation Products | D-(+)-Carvone Tosylhydrazone-->2-Cyclohexen-1-one, 2,6-dimethyl-5-(1-methylethenyl)-, (5S)- |
