Select a region with no data or 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. Squirrel monkeys have also been found to be able to discriminate between carvone enantiomers. Technology, Office of Data Notice: This spectrum may be better viewed with a Javascript [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 Please see the following for information about 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. and Informatics, NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data). [1] Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi) and dill. Both carvones are used in the food and flavor industry. L-carvone is a plant-derived pesticide that is approved for use in many countries. Data Program, but require an annual fee to access. The data are manually curated and of the highest quality. Standard Reference Data Act. 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 ChEBI Name carvone: ChEBI ID CHEBI:38265: Definition A p-menthane ... IUPAC Names 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one p-mentha-1(6),8-dien-2-one Synonyms Sources 1-carvone ChEBI 2-methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-one ChEBI 2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one ChEBI 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone ChEBI 2-methyl-5-isopropenyl-2 … available from the NIST/EPA/NIH Mass Spectral Library. Find out how LUMITOS supports you with online marketing. uses its best efforts to deliver a high quality copy of the © 1997-2020 LUMITOS AG, All rights reserved, https://www.chemeurope.com/en/encyclopedia/Carvone.html, Your browser is not current. intended to imply recommendation or endorsement by the National 1.) Thank you to ChemDoodle for providing this functionality! Draw your molecule in the sketcher below, and the IUPAC name will be displayed here for free. Not all enantiomers have distinguishable odors. its accompanying search program. GENERAL INFORMATION for L-carvone . However, NIST makes no warranties to that effect, and NIST 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. © 2018 by the U.S. Secretary of Commerce Its mirror image, R-(–)-carvone, smells like spearmint. Formula: C 10 H 14 O; Molecular weight: 150.2176; IUPAC Standard InChI: Spectral Data. NIST Standard Reference All mass spectra in this site (plus many more) are been selected on the basis of sound scientific judgment. Featured suppliers/resources for 1-Carvone List your site here. Found naturally in many essential oils, it is most abundant in the oils from seeds of caraway (Carum carvi) and dill. ChemDoodle Web Components. jcamp-dx.js and Data compilation copyright Carvone mass spectral data can be found in a separate interface. Use or mention of technologies or programs in this web site is not Find out more about the company LUMITOS and our team. This entity has been manually annotated by the ChEBI Team. Standard Reference Data Act. for carvone . Carvone is available inexpensively in both enantiomerically pure forms, making it an attractive starting material for the asymmetric total synthesis of natural products. S-(+)-Carvone has shown a suppressant effect against high-fat diet induced weight gain in mice. [1] It was originally called carvol by Schweizer. 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. Carvone mass spectral data can be found in a separate interface. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE. To use all functions of this page, please activate cookies in your browser. (e.g.. NIST Mass Spectrometry Data Center, 1990. ID: Reference343 Other Names: 6,8-p-Menthadien-2-one; 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one . Copyright for NIST Standard Reference Data is governed by Systematic / IUPAC Name: 5-Isopropenyl-2-methyl-2-cyclohexen-1-one. Wrigley's Spearmint Gum is gum soaked in R-(–)-carvone and powdered with sugar. As the compound most responsible for the flavor of caraway, dill and spearmint, carvone has been used for millennia in food. (, 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. The biosynthesis of carvone is by oxidation of limonene. As an α,beta;-unsaturated ketone, carvone undergoes conjugate additions of nucleophiles. The following components were used in generating the plot: Additonal code used was developed at NIST: and HTML 5 enabled browser. Data from NIST Standard Reference Database 69: The National Institute of Standards and Technology (NIST) the library and shall not be liable for any damage that may result from (−)-carvone (CHEBI:15400) is a carvone (CHEBI:38265) (+)-carvone (CHEBI:15399) is a carvone (CHEBI:38265) IUPAC Names 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one The following software generates IUPAC names for molecules and powers this website. If you continue browsing our websites, we'll assume that you are happy to receive all cookies on mzCloud.org. [2], Carvone forms two mirror image forms or enantiomers: S-(+)-carvone smells like caraway. Data Program, but require an annual fee to access. been selected on the basis of sound scientific judgment. with the development of data collections included in the The purpose of the fee is to recover costs associated With hydrogen peroxide the epoxide 8 is formed. Oxidation of carvone can also lead to a variety of products. such sites. Institute of Standards and Technology, nor is it intended to imply Formula: C 10 H 14 O; Molecular weight: 150.2176; IUPAC Standard InChI: Copyright for NIST Standard Reference Data is governed by All rights reserved. by the U.S. Secretary of Commerce on behalf of the U.S.A. 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. PIN (Preferred Identification Name) - IUPAC name : 5-isopropenyl-2-methylcyclohex-2-en-1-one : CAS name : 2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one : Other status information - Relevant Environmental Water Quality Standards - Herbicide Resistance Classification (HRAC) [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. 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 [citation needed]. spectrum (can be printed in landscape orientation). Enter the desired X axis range 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. There are three double bonds in carvone capable of reduction; the product of reduction depends on the reagents and conditions used. Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. Carvone may be cleaved using ozone followed by steam, giving dilactone 9, while KMnO4 gives 10. [8] (4R,6S)-(–)-carveol is also formed as a minor product via reduction by NADPH. (2016) An international database for pesticide risk assessments and management. jcamp-plot.js. It has a low aqueous solubility and is volatile. All rights reserved. errors or omissions in the Database. Categories: Terpenes and terpenoids | Ketones. on behalf of the United States of America. It would be difficult to assign unique individual names that we could remember. It has a low mammalian oral toxicity and is a recognised irritant. Follow the links above to find out more about the data An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. [9] This mainly occurs in the liver and involves cytochrome P450 oxidase and (+)-trans-carveol dehydrogenase. The data are manually curated and of the highest quality. (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] 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 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. However, NIST makes no warranties to that effect, and NIST that these items are necessarily the best available for the purpose. Go To: Top, Mass spectrum (electron ionization), Notes, Go To: Top, Mass spectrum (electron ionization), References. When naming organic compounds, the IUPAC (International Union of Pure and Applied Chemistry) nomenclature (naming scheme) is used. NIST subscription sites provide data under the source: Wikipedia.org. Carvone is a member of a family of chemicals called terpenoids. errors or omissions in the Database. Description: A fungicide and plant growth regulator often used as a potato sprouting inhibitor . Biology Laboratory | Terms of use. ChemDoodle 2D. Read what you need to know about our industry portal chemeurope.com. 4.3 IUPAC naming and formulae (ESCKG) What is IUPAC naming? Zinc and acetic acid reduce carvone to give dihydrocarvone (4). 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) NIST Standard Reference (-)-Carvone. The resulting enolate can then be allylated using allyl bromide to give ketone 11.