(-)-Caryophyllene oxide - ≥99%(GC), sum of enantiomers , CAS No.1139-30-6

CAS: 1139-30-6 Cat. No.: C345753 Peso molecular: 220.35 Número EC: 214-519-7

GRADE & PURITY ≥99%(GC), sum of enantiomers

Synonyms

(-)Carophyllene oxide | [1R-(1R*,4R*,6R*,10S*)]- (-)-Epoxydihydrocaryophyllene (-)-<>-Caryophyllene epoxide (-)-<>-Caryophyllene oxide 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane | C16908 | (-)-Caryophyllene oxide, >=99.0

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Descripción general

(−)-Caryophyllene oxide or β-caryophyllene oxide (BCPO) is a natural plant compound, bicyclic sesquiterpene, and oxidation derivative of β-caryophyllene (BCP).  It has a strong wooden odor.  BCPO is commonly found in many food and spice plants and essential oils, such as basil, salvia, and Syzygium cordatum. It is widely used as a cosmetic and food additive. 

Application

(−)-Caryophyllene oxide has been used:

as an antimicrobial agent to study its effects against Gram-positive, Gram-negative and yeast strains 

as a commercial standard to perform quantification analysis of constitutes from Marchantia polymorpha extracts using gas chromatography with flame-ionization detection (GC-FID) 

as a reference standard to analyze the enantiomeric ratios of Achillea ligustica essential oil constituents using gas chromatography-mass spectrometry (GC-MS) 

Specifications

Sinónimos

(-)Carophyllene oxide | [1R-(1R*, 4R*, 6R*, 10S*)]- (-)-Epoxydihydrocaryophyllene (-)-<>-Caryophyllene epoxide (-)-<>-Caryophyllene oxide 4, 11, 11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4, 6))dodecane | C16908 | (-)-Caryophyllene oxide, >=99.0

Especificaciones y pureza

≥99%(GC), sum of enantiomers

Mecanismos bioquímicos y fisiológicos

β-caryophyllene oxide is a potent anti-cancer agent which also exerts antioxidant, anti-inflammatory, and antiviral properties.It is a strong inhibitor of drug-metabolizing enzyme cytochromes P4503A (CYP3A) activities both in rat and human hepatic microso

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Protected from light, Desiccated

Enviado en

Wet ice

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Pureza

≥99%(GC)

Nombres e identificadores

• Pubchem Sid: 488191998
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488191998
• Sonrisas canónicas: CC1(CC2C1CCC3(C(O3)CCC2=C)C)C
• IUPAC Name: (1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane
• InChIKey: NVEQFIOZRFFVFW-RGCMKSIDSA-N
• INCHI: 1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1
• Isómeros SMILES: C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2
• WGK Alemania: 2
• RTECS: RP5530000
• Peso molecular: 220.35
• Reaxy-Rn: 148213
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=148213&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Sesquiterpenoids
• Alternative Parents: Oxacyclic compounds Epoxides Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Caryophyllane sesquiterpenoid - Sesquiterpenoid - Oxacycle - Organoheterocyclic compound - Ether - Oxirane - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
• External Descriptors: Caryophyllane sesquiterpenoids

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 (humanos)

TRPV1 Tclin Vanilloid receptor (8273 Activities)

Discover Target: TRPV1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HL (112 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Chlamydia pneumoniae (241 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Tetranychus urticae (2600 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PC-12 (7051 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ileum (29 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Jejunum (38 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Light sensitive
• Punto de fusión (°C): 62-63° C (lit.)
• Peso molecular: 220.350 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 220.183 Da
• Monoisotopic Mass: 220.183 Da
• Topological Polar Surface Area: 12.500 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 330.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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

1. Pengfei Yang, Lingqi Kong, Qiongbo Wang, Qiang Liu, Xiujin Duan, Chen Hu, Zhengbo Feng, Qi Yang, Huabo Jv.  (2026)  Analysis of volatile compounds in Aglaia odorata flower extracts with different possessing methods by HS-SPME-GC-MS and E-nose.  Frontiers in Chemistry,      [PMID:41867951] [10.3389/fchem.2026.1746408]