Data compilation copyright Categories: Terpenes and terpenoids | Ketones. [3] The fact that the two enantiomers are perceived as smelling differently is proof that olfactory receptors must contain chiral groups, allowing them to respond more strongly to one enantiomer than to the other. For example, carvone reacts with lithium dimethylcuprate to place a methyl group trans to the isopropenyl group with good stereoselectivity. This site uses cookies. on behalf of the United States of America. uses its best efforts to deliver a high quality copy of the [2], Carvone forms two mirror image forms or enantiomers: S-(+)-carvone smells like caraway. Biology Laboratory, InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3, (−)-carvone Copyright © 2013 - 2020 HighChem LLC, Slovakia, mzCloud is a trademark of HighChem LLC, Slovakia, 5-Isopropenyl-2-methyl-2-cyclohexen-1-one, 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one, InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3. R-(-)-Carvone is also used for air freshening products and, like many essential oils, oils containing carvones are used in aromatherapy and alternative medicine. PIN (Preferred Identification Name) - IUPAC name (R)-5-isopropenyl-2-methylcyclohex-2-en-1-one : CAS name (R)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one : Other status information - Relevant Environmental Water Quality Standards - Herbicide Resistance Classification (HRAC) Formula: C 10 H 14 O; Molecular weight: 150.2176; IUPAC Standard InChI: such sites. Technology, Office of Data Its mirror image, R-(–)-carvone, smells like spearmint. jcamp-dx.js and the library and Please see the following for information about Squirrel monkeys have also been found to be able to discriminate between carvone enantiomers. The two forms are also referred to by older names, with dextro-, d- referring to S-carvone, and laevo-, l- referring to R-carvone. by the U.S. Secretary of Commerce on behalf of the U.S.A. A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. This entity has been manually annotated by the ChEBI Team. (2016) An international database for pesticide risk assessments and management. Squirrel monkeys have also been found to be able to discriminate between carvone enantiomers.[4]. To name alkanes by the IUPAC system and write formulas for alkanes given IUPAC names; As noted in previously, the number of isomers increases rapidly as the number of carbon atoms increases. An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. Name Carvon Andere Namen p-Mentha-6,8-dien-2-on; 1-Methyl-4-isopropenyl-6-cyclohexen-2-on; Summenformel: C 10 H 14 O Externe Identifikatoren/Datenbanken The fact that the two enantiomers are perceived as smelling differently is proof that olfactory receptorsmust contain chiral groups, allowing them to respond more strongly to one enantiomer than to the other. Carvone may be cleaved using ozone followed by steam, giving dilactone 9, while KMnO4 gives 10. As the compound most responsible for the flavor of caraway, dill and spearmint, carvone has been used for millennia in food. 2D Chemical Drawing, Publishing and Informatics. the Caraway was used for medicinal purposes by the ancient Romans,[2] but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841. There are 3 pentanes, 5 hexanes, 9 heptanes, and 18 octanes. (, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one, 2-methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone, 5-isopropenyl-2-methylcyclohex-2-en-1-one. Data from NIST Standard Reference Database 69: The National Institute of Standards and Technology (NIST) Database and to verify that the data contained therein have (ESCKH) In order to give compounds a name, certain rules must be followed. in these sites and their terms of usage. © 1997-2020 LUMITOS AG, All rights reserved, https://www.chemeurope.com/en/encyclopedia/Carvone.html, Your browser is not current. Oxidation of carvone can also lead to a variety of products. Zinc and acetic acid reduce carvone to give dihydrocarvone (4). InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1, National Institute of Standards and There are three double bonds in carvone capable of reduction; the product of reduction depends on the reagents and conditions used. [2] It also occurs to the extent of about 40-60% in dill seed oil (from Anethum graveolens), and also in mandarin orange peel oil. The two form… Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. and HTML 5 enabled browser. NIST subscription sites provide data under the Not all enantiomers have distinguishable odors. Notice: This spectrum may be better viewed with a Javascript with the development of data collections included in shall not be liable for any damage that may result from GENERAL INFORMATION for L-carvone . Biology Laboratory | Terms of use. errors or omissions in the Database. For example, (S)-(+)-carvone was used to begin a 1998 synthesis of the terpenoid quassin[7]: In the body, in vivo studies indicate that both enantiomers of carvone are mainly metabolized into dihydrocarvonic acid, carvonic acid and uroterpenolone. There is limited data availablity regarding its persistent in soil andwater systems. Both carvones are used in the food and flavor industry. Go To: Top, Mass spectrum (electron ionization), Notes, Go To: Top, Mass spectrum (electron ionization), References. Data from NIST Standard Reference Database 69: The National Institute of Standards and Technology (NIST) Goldschmidt and Zűrrer identified it as a ketone related to limonene, and the structure was finally elucidated by Wagner in 1894.[6]. Description: A fungicide and plant growth regulator often used as a potato sprouting inhibitor . As an α,beta;-unsaturated ketone, carvone undergoes conjugate additions of nucleophiles. View image of digitized Database and to verify that the data contained therein have MPV reduction using propan-2-ol and aluminium isopropoxide effects reduction of the carbonyl group only to provide carveol (5); a combination of sodium borohydride and CeCl3 (Luche reduction) is also effective. Draw your molecule in the sketcher below, and the IUPAC name will be displayed here for free. The data are manually curated and of the highest quality. [citation needed]. Select a region with no data or The following software generates IUPAC names for molecules and powers this website. Aecochem Corp: Manufacturer : China: Your reliable partner in Chemical business,Major in the HIGH quality Fine and Specialty chemical produce and supply(Our clients like BASF,CHEMO,Brenntag,etc. (-)-Carvone. With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter. shall not be liable for any damage that may result from Carvone is available inexpensively in both enantiomerically pure forms, making it an attractive starting material for the asymmetric total synthesis of natural products. with the development of data collections included in the © 2018 by the U.S. Secretary of Commerce errors or omissions in the Database. All rights reserved. Ecotoxicity tends to be low to moderate for most species. such sites. ChemDoodle Web Components. ID: Reference343 Other Names: 6,8-p-Menthadien-2-one; 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one . 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one, Class: on behalf of the United States of America. R-(−)-Carvone is also used for air freshening products and, like many essential oils, oils containing carvones are used in aromatherapy and alternative medicine. Carvone forms two mirror image forms or enantiomers: S-(+)-carvone smells like caraway. Not all enantiomers have distinguishable odors. A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. Find out how LUMITOS supports you with online marketing. The data are manually curated and of the highest quality. NIST Standard Reference available from the NIST/EPA/NIH Mass Spectral Library. and Informatics, NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data). Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director. HTML 5 canvas support. InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1, National Institute of Standards and Carvone is a member of a family of chemicals called terpenoids. NIST Standard Reference The dextro-form is obtained practically pure by the fractional distillation of caraway oil; the laevo-form from the oils containing it, by first forming its addition compound with hydrogen sulfide, decomposing this by potassium hydroxide in ethanol, and distilling the product in a current of steam. Copyright for NIST Standard Reference Data is governed by Systematic / IUPAC Name: 5-Isopropenyl-2-methyl-2-cyclohexen-1-one, Other Names: (e.g.. NIST Mass Spectrometry Data Center, 1990. its accompanying search program. The purpose of the fee is to recover costs associated It may be synthetically prepared from limonene nitrosochloride, alcoholic converting this compound into 1-carvoxime, which on boiling with dilute sulfuric acid yields l-carvone. Select a region with data to zoom. S-(+)-Carvone is also used to prevent premature sprouting of potatoes during storage, being marketed in the Netherlands for this purpose under the name Talent. Hydrazine and potassium hydroxide give limonene (6) via a Wolff-Kishner reduction. It has a low aqueous solubility and is volatile. Thank you to ChemDoodle for providing this functionality! (5R)-5-Isopropenyl-2-methyl-2-cyclohex en-1-on [German] [ACD/IUPAC Name] More... (5R)-5-Isopropenyl- 2-methyl-2-cyclohex en-1-one [ACD/IUPAC Name] Formula: C 10 H 14 O; Molecular weight: 150.2176; IUPAC Standard InChI: R-(–)-Carvone is present at levels greater than 51% in spearmint oil (Mentha spicata), which is produced on a scale of around 1500 tonnes annually. and Informatics, NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data), NIST Mass Spectrometry Data Center, William E. Wallace, director, Modified by NIST for use in this application. Use or mention of technologies or programs in this web site is not