L(-)-Carvone - ≥99% , CAS No.6485-40-1

CAS: 6485-40-1 Cat. No.: C117707 Peso molecular: 150.22 Beilstein Registry Number: 2206714 Número EC: 229-352-5

GRADE & PURITY ≥99%

Synonyms

(R)-CARVONE (CONSTITUENT OF MYRRH) | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)- | AKOS006343214 | Q-103514 | DTXCID5021413 | DTXSID7041413 | EN300-298834 | L-Carvone, >=97%, FCC, FG | (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one | 07V

Storage

Argon charged,Room temperature

Shipped In

Normal

Descripción general

(R)-(-)-Carvone is a monoterpenoid. Its ozonolysis in the gaseous phase has been proposed. Aldehydes (formaldehyde) and biradicals were obtained as the major products. It participates in the diastereoselective synthesis of homochiral octalones.

(R)-(-)-Carvone may be employed as starting reagent for the synthesis of enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, a useful intermediate formed during the synthesis of terpenoids. It may be employed as starting reagent for the synthesis of differently protected (4S,6R,7R)-trihydroxy-1-octyne derivatives.

Specifications

Sinónimos

(R)-CARVONE (CONSTITUENT OF MYRRH) | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)- | AKOS006343214 | Q-103514 | DTXCID5021413 | DTXSID7041413 | EN300-298834 | L-Carvone, >=97%, FCC, FG | (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one | 07V

Especificaciones y pureza

≥99%

Condiciones de almacenamiento de almacenamiento

Argon charged, Room temperature

Enviado en

Normal

Pureza

≥99%

Nombres e identificadores

• Pubchem Sid: 488189748
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189748
• Sonrisas canónicas: CC1=CCC(CC1=O)C(=C)C
• IUPAC Name: (5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
• InChIKey: ULDHMXUKGWMISQ-SECBINFHSA-N
• 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
• Isómeros SMILES: CC1=CC[C@H](CC1=O)C(=C)C
• WGK Alemania: 2
• RTECS: OS8650000
• Peso molecular: 150.22
• Beilstein: 2206714
• Reaxy-Rn: 1364206
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1364206&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Menthane monoterpenoids
• Alternative Parents: Monocyclic monoterpenoids Cyclohexenones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: P-menthane monoterpenoid - Monocyclic monoterpenoid - Cyclohexenone - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Descripción: This compound 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.
• External Descriptors: Menthane monoterpenoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (no humanos)

Spodoptera littoralis (798 Activities)

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Meloidogyne incognita (862 Activities)

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Mus musculus (284745 Activities)

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Tribolium castaneum (596 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Miscible with alcohol, ether, chloroform, propylene glycol and mineral oils. Immiscible with water and glycerol.
• Sensibilidad: Light and air sensitive
• Índice de refracción: 1.495-1.502
• Rotación específica [α]: -61.5 ° (neat)
• Punto de inflamación (°F): 201.2 °F
• Punto de inflamación (°C): 88°C
• Punto de ebullición (°C): 227-230°C
• Peso molecular: 150.220 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 150.104 Da
• Monoisotopic Mass: 150.104 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 223.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

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2. Jie Chen, Xin Hao, Ruina Tan, Yang Li, Bowen Wang, Jialiang Pan, Wei Ma, Ling Ma.  (2022)  Functional Study on Cytochrome P450 in Response to L(−)-Carvone Stress in Bursaphelenchus xylophilus.  Genes,  13  (11): (1956).  [PMID:36360193] [10.3390/genes13111956]

3. Shijin Wu, Bijiao Wang, Hongde Yan.  (2022)  Semi-rational protein engineering of a novel ene-reductase from Galdieria sulphuraria for asymmetric reduction of (R)-carvone and ketoisophorone.  BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY,  70  (2): (697-706).  [PMID:35906824] [10.1002/bab.2391]

4. Jinhao Zhao, Minmin Liang, Zhongyan Wang, Yanyan Zhao, Jingli Cheng, Yongjun Du.  (2022)  Evaluation and optimization of blends for attracting Trichogramma dendrolimi based on semiochemicals mediating tritrophic interactions in the orchard habitat.  BIOLOGICAL CONTROL,      [PMID:] [10.1016/j.biocontrol.2022.104998]

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6. Yujiao Cheng, Guijie Li, Houjiu Wu, Linhua Huang, Hua Wang.  (2021)  Identification of Light-Induced Key Off-Flavors in Ponkan Mandarin Juice Using MDGC-MS/O and GC–MS/PFPD.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:34784211] [10.1021/acs.jafc.1c05465]

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9. Beitao Liu, Jiahui Li, Cijian Zhang, Yibo Wang, Xigao Jian, Zhihuan Weng.  (2024)  “Polymer to polymer” recycling and body-temperature triggered shape memory of a carvone-based epoxy thermoset system achieved using a thiol-Michael covalent adaptable network.  Journal of Materials Chemistry A,      [PMID:] [10.1039/D4TA03378G]

10. Shijin Wu, Xiaojing Ma, Hongde Yan.  (2024)  Identification and characterization of an ene-reductase from Corynebacterium casei.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38428763] [10.1016/j.ijbiomac.2024.130427]

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