(S)-Carvone (BioDeep_00000014523)

 

Secondary id: BioDeep_00000405588, BioDeep_00000861365

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


D-Carvone 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one

化学式: C10H14O (150.1044594)
中文名称: 右旋香芹酮, (S)-(+)-香芹酮, 右旋香芹酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.09%

分子结构信息

SMILES: C=C(C)[C@H]1CC=C(C)C(=O)C1
InChI: 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

描述信息

Carvone, with R and S isomers, also known as carvol or limonen-6-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886 , 2477620 ). Carvone may help in the management of diseases (PMID:30374904) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792) and patients with epilepsy (PMID:31239862). It also has been successfully used as a biopesticide (PMID:30250476).
D-carvone appears as pale yellow or colorless liquid. (NTP, 1992)
(+)-carvone is a carvone having (S) configuration. It is an enantiomer of a (-)-carvone.
d-Carvone is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available.
See also: Caraway Oil (part of).
A carvone having (S) configuration.

同义名列表

62 个代谢物同义名

D-Carvone 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5S)-; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-; (+)-Carvone, certified reference material, TraceCERT(R); (5S)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one; (5S)-2-methyl-5-(1-methylethenyl)cyclohex-2-en-1-one; (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one; (S)-2-methyl-5-(1-methylethenyl)-2-Cyclohexen-1-one; (5S)-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-one; (S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one; 2-Methyl-4-(1 -methylethenyl)-2-cyclohexene-1 -one; (5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one; (S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one; 5-Isopropenyl-2-methyl-2-cyclohexen-1-one, (S)-; (S)-2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone; 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one; (S)-5-isopropenyl-2-methylcyclohex-2-en-1-one; d-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; (S)-5-Isopropenyl-2-methyl-2-cyclohexenone; (S)-d-p-Mentha-6,8,(9)-dien-2-one; p-Mentha-6,8-dien-2-one, (S)-(+)-; (+)-Carvone, analytical standard; (S)-(+)-p-Mentha-6,8-dien-2-one; (4S)-p-mentha-1(6),8-dien-2-one; d-p-Mentha-6,8,(9)-dien-2-one; d-p-Mentha-6,8(9)-dien-2-one; (S)-(+)-Carvone, 96\\%; D-Carvone, >=96\\%, FG; d-Carvone (natural); CARVONE D-FORM [MI]; (+)-CARVONE [FCC]; (+)-(4S)-carvone; (+)-(S)-Carvone; UNII-4RWC1CMS3X; (S)-(+)-Carvone; CARVONE D-FORM; S-(+)-carvone; Carvone, (+)-; D-(+)-Carvone; Tox21_201441; D(+)-Carvone; (4S)-carvone; Tox21_302743; S(+)-Carvone; CARVONE, D-; (+)-Carvone; (S)-Carvone; CARVONE D-; (+)carvone; D-?Carvone; 4RWC1CMS3X; d-Carvone; s-carvone; AI3-39004; d-carvon; D-CARVOL; CARVONE; Carvol; Talent; 0WU; (+)-(S)-Carvone; d-Carvone



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(2)

BioCyc(1)

PlantCyc(1)

代谢反应

8 个相关的代谢反应过程信息。

Reactome(2)

  • Olfactory Signaling Pathway: GTP + odorant:Olfactory Receptor:GNAL:GDP:GNB1:GNG13 ⟶ GDP + odorant:Olfactory Receptor:GNAL:GTP:GNB1:GNG13
  • Sensory Perception: GTP + odorant:Olfactory Receptor:GNAL:GDP:GNB1:GNG13 ⟶ GDP + odorant:Olfactory Receptor:GNAL:GTP:GNB1:GNG13

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

119 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Hwa-Jeong Yeom, Jae Soon Kang, Gil-Hah Kim, Il-Kwon Park. Insecticidal and acetylcholine esterase inhibition activity of Apiaceae plant essential oils and their constituents against adults of German cockroach (Blattella germanica). Journal of agricultural and food chemistry. 2012 Jul; 60(29):7194-203. doi: 10.1021/jf302009w. [PMID: 22746406]
  • Sonja Rentzsch, Dagmara Podzimska, Antje Voegele, Madeleine Imbeck, Kerstin Müller, Ada Linkies, Gerhard Leubner-Metzger. Dose- and tissue-specific interaction of monoterpenes with the gibberellin-mediated release of potato tuber bud dormancy, sprout growth and induction of α-amylases and β-amylases. Planta. 2012 Jan; 235(1):137-51. doi: 10.1007/s00425-011-1501-1. [PMID: 21858448]
  • Karina Caballero-Gallardo, Jesús Olivero-Verbel, Elena E Stashenko. Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst. Journal of agricultural and food chemistry. 2011 Mar; 59(5):1690-6. doi: 10.1021/jf103937p. [PMID: 21291237]
  • S Jana, G S Shekhawat. Anethum graveolens: An Indian traditional medicinal herb and spice. Pharmacognosy reviews. 2010 Jul; 4(8):179-84. doi: 10.4103/0973-7847.70915. [PMID: 22228959]
  • Patricia Escobar, Sandra Milena Leal, Laura Viviana Herrera, Jairo Rene Martinez, Elena Stashenko. Chemical composition and antiprotozoal activities of Colombian Lippia spp essential oils and their major components. Memorias do Instituto Oswaldo Cruz. 2010 Mar; 105(2):184-90. doi: 10.1590/s0074-02762010000200013. [PMID: 20428679]
  • J R-M Brown, I P Thompson, G I Paton, A C Singer. Enhanced biotransformation of TCE using plant terpenoids in contaminated groundwater. Letters in applied microbiology. 2009 Dec; 49(6):769-74. doi: 10.1111/j.1472-765x.2009.02738.x. [PMID: 19843209]
  • Damião P de Sousa, Genival A S Júnior, Luciana N Andrade, Flávia R Calasans, Xirley P Nunes, José M Barbosa-Filho, Josemar S Batista. Structure and spasmolytic activity relationships of monoterpene analogues found in many aromatic plants. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Nov; 63(11-12):808-12. doi: 10.1515/znc-2008-11-1205. [PMID: 19227827]
  • Wayne L Silver, Tod R Clapp, Leslie M Stone, Sue C Kinnamon. TRPV1 receptors and nasal trigeminal chemesthesis. Chemical senses. 2006 Nov; 31(9):807-12. doi: 10.1093/chemse/bjl022. [PMID: 16908491]
  • Jun-Hyung Tak, Hyun-Kyung Kim, Seung-Hwan Lee, Young-Joon Ahn. Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae). Pest management science. 2006 Jun; 62(6):551-7. doi: 10.1002/ps.1212. [PMID: 16602084]
  • Young-Su Jang, Young-Cheol Yang, Dal-Soon Choi, Young-Joon Ahn. Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae). Journal of agricultural and food chemistry. 2005 Oct; 53(20):7892-8. doi: 10.1021/jf051127g. [PMID: 16190647]
  • Abdel-Fattah A Khalaf. Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson. Journal of the Egyptian Society of Parasitology. 2004 Apr; 34(1):227-37. doi: . [PMID: 15125529]
  • Simon Muhoho Njoroge, Hiroyuki Ukeda, Masayoshi Sawamura. Changes of the volatile profile and artifact formation in Daidai (Citrus aurantium) cold-pressed peel oil on storage. Journal of agricultural and food chemistry. 2003 Jul; 51(14):4029-35. doi: 10.1021/jf021215q. [PMID: 12822942]
  • Leopold Jirovetz, Gerhard Buchbauer, Albena S Stoyanova, Evgenii V Georgiev, Stanka T Damianova. Composition, quality control, and antimicrobial activity of the essential oil of long-time stored dill (Anethum graveolens L.) seeds from Bulgaria. Journal of agricultural and food chemistry. 2003 Jun; 51(13):3854-7. doi: 10.1021/jf030004y. [PMID: 12797755]
  • Paul McGeady, Daniel L Wansley, David A Logan. Carvone and perillaldehyde interfere with the serum-induced formation of filamentous structures in Candida albicans at substantially lower concentrations than those causing significant inhibition of growth. Journal of natural products. 2002 Jul; 65(7):953-5. doi: 10.1021/np010621l. [PMID: 12141851]
  • Paola Bonsi, Flavia Zucco, Annalaura Stammati. Two in vitro models for gas-phase exposure to volatile compounds. Alternatives to laboratory animals : ATLA. 2002 Mar; 30(2):241-7. doi: 10.1177/026119290203000210. [PMID: 11971752]
  • C Ghelardini, N Galeotti, G Mazzanti. Local anaesthetic activity of monoterpenes and phenylpropanes of essential oils. Planta medica. 2001 Aug; 67(6):564-6. doi: 10.1055/s-2001-16475. [PMID: 11509984]
  • W Jäger, M Mayer, G Reznicek, G Buchbauer. Percutaneous absorption of the montoterperne carvone: implication of stereoselective metabolism on blood levels. The Journal of pharmacy and pharmacology. 2001 May; 53(5):637-42. doi: 10.1211/0022357011775965. [PMID: 11370703]