Caryophyllene

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MedKoo CAT#: 596940

CAS#: 87-44-5

Description: Caryophyllene is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.


Chemical Structure

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Caryophyllene
CAS# 87-44-5

Theoretical Analysis

MedKoo Cat#: 596940
Name: Caryophyllene
CAS#: 87-44-5
Chemical Formula: C15H24
Exact Mass: 204.1878
Molecular Weight: 204.35
Elemental Analysis: C, 88.16; H, 11.84

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Caryophyllene; AI3-36121; CCRIS 8094; E-Caryophyllene;

IUPAC/Chemical Name: (1R,9S,E)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene

InChi Key: NPNUFJAVOOONJE-GFUGXAQUSA-N

InChi Code: InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1

SMILES Code: C=C1CC/C=C(C)/CC[C@@]2([H])C(C)(C)C[C@]12[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 204.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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6: Tang Y, Wu Y, Hu J, Sun C, Cao Y, Li Y, Xie F, Zeng T, Zhou B, Du J. Nature-Inspired Bioorthogonal Reaction: Development of β-Caryophyllene as A Chemical Reporter in Tetrazine Ligation. Bioconjug Chem. 2018 May 31. doi: 10.1021/acs.bioconjchem.8b00283. [Epub ahead of print] PubMed PMID: 29851464.

7: George MJ, Njobeh PB, Gbashi S, Adegoke GO, Dubery IA, Madala NE. Rapid Screening of Volatile Organic Compounds from Aframomum danielli Seeds Using Headspace Solid Phase Microextraction Coupled to Gas Chromatography Mass Spectrometry. Int J Anal Chem. 2018 Apr 19;2018:8976304. doi: 10.1155/2018/8976304. eCollection 2018. PubMed PMID: 29849643; PubMed Central PMCID: PMC5933046.

8: Yan DH, Song X, Li H, Luo T, Dou G, Strobel G. Antifungal Activities of Volatile Secondary Metabolites of Four Diaporthe Strains Isolated from Catharanthus roseus. J Fungi (Basel). 2018 May 30;4(2). pii: E65. doi: 10.3390/jof4020065. PubMed PMID: 29848985.

9: Baron EP, Lucas P, Eades J, Hogue O. Patterns of medicinal cannabis use, strain analysis, and substitution effect among patients with migraine, headache, arthritis, and chronic pain in a medicinal cannabis cohort. J Headache Pain. 2018 May 24;19(1):37. doi: 10.1186/s10194-018-0862-2. PubMed PMID: 29797104; PubMed Central PMCID: PMC5968020.

10: Lee HR, Lee SC, Lee DH, Jung M, Kwon JH, Huh MJ, Kim DS, Lee JE, Park IK. Identification of Aggregation-Sex Pheromone of the Korean Monochamus alternatus (Coleoptera: Cerambycidae) Population, the Main Vector of Pine Wood Nematode. J Econ Entomol. 2018 May 19. doi: 10.1093/jee/toy137. [Epub ahead of print] PubMed PMID: 29788181.

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12: Di Napoli M, Varcamonti M, Basile A, Bruno M, Maggi F, Zanfardino A. Anti-Pseudomonas aeruginosa activity of hemlock (Conium maculatum, Apiaceae) essential oil. Nat Prod Res. 2018 May 21:1-5. doi: 10.1080/14786419.2018.1477151. [Epub ahead of print] PubMed PMID: 29781307.

13: Huang GZ, Liu JT, Zhou JJ, Wang Q, Dong JZ, Zhang YJ, Li XC, Li J, Gu SH. Expressional and functional comparisons of two general odorant binding proteins in Agrotis ipsilon. Insect Biochem Mol Biol. 2018 Jul;98:34-47. doi: 10.1016/j.ibmb.2018.05.003. Epub 2018 May 17. PubMed PMID: 29778539.

14: Quan M, Liu QZ, Liu ZL. Identification of Insecticidal Constituents from the Essential Oil from the Aerial Parts Stachys riederi var. japonica. Molecules. 2018 May 17;23(5). pii: E1200. doi: 10.3390/molecules23051200. PubMed PMID: 29772795.

15: Han X, Beaumont C, Rodriguez D, Bahr T. Black pepper (Piper nigrum) essential oil demonstrates tissue remodeling and metabolism modulating potential in human cells. Phytother Res. 2018 May 17. doi: 10.1002/ptr.6110. [Epub ahead of print] PubMed PMID: 29770504.

16: He Q, Wang W, Zhu L. Larvicidal activity of Zanthoxylum acanthopodium essential oil against the malaria mosquitoes, Anopheles anthropophagus and Anopheles sinensis. Malar J. 2018 May 15;17(1):194. doi: 10.1186/s12936-018-2341-2. PubMed PMID: 29764438; PubMed Central PMCID: PMC5952513.

17: Masoudi S. Volatile Constituents from Different Parts of Three Lamiacea Herbs from Iran. Iran J Pharm Res. 2018 Winter;17(1):365-376. PubMed PMID: 29755567; PubMed Central PMCID: PMC5937106.

18: Martínez LC, Plata-Rueda A, da Silva Neves G, Cossolin JF, Dos Santos MH, Zanuncio JC, Serrão JE. Morphology, ultrastructure, and chemical compounds of the osmeterium of Heraclides thoas (Lepidoptera: Papilionidae). Protoplasma. 2018 May 11. doi: 10.1007/s00709-018-1261-x. [Epub ahead of print] PubMed PMID: 29752568.

19: Figueiredo PLB, Silva RC, da Silva JKR, Suemitsu C, Mourão RHV, Maia JGS. Chemical variability in the essential oil of leaves of Araçá (Psidium guineense Sw.), with occurrence in the Amazon. Chem Cent J. 2018 May 10;12(1):52. doi: 10.1186/s13065-018-0428-z. PubMed PMID: 29748791; PubMed Central PMCID: PMC5945564.

20: Andrade-Ochoa S, Correa-Basurto J, Rodríguez-Valdez LM, Sánchez-Torres LE, Nogueda-Torres B, Nevárez-Moorillón GV. In vitro and in silico studies of terpenes, terpenoids and related compounds with larvicidal and pupaecidal activity against Culex quinquefasciatus Say (Diptera: Culicidae). Chem Cent J. 2018 May 10;12(1):53. doi: 10.1186/s13065-018-0425-2. PubMed PMID: 29748726; PubMed Central PMCID: PMC5945571.