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MedKoo Cat#: 596940 | Name: Caryophyllene

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Caryophyllene
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 currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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
More Info

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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Br Poult Sci. 2018 Jun 6. doi: 10.1080/00071668.2018.1483577. [Epub ahead of print] PubMed PMID: 29873243. 4: Cao JQ, Guo SS, Wang Y, Pang X, Geng ZF, Du SS. Toxicity and repellency of essential oil from Evodia lenticellata Huang fruits and its major monoterpenes against three stored-product insects. Ecotoxicol Environ Saf. 2018 Sep 30;160:342-348. doi: 10.1016/j.ecoenv.2018.05.054. Epub 2018 May 29. PubMed PMID: 29857238. 5: Mohamed K, Zine K, Fahima K, Abdelfattah E, Sharifudin SM, Duduku K. NiO nanoparticles induce cytotoxicity mediated through ROS generation and impairing the antioxidant defense in the human lung epithelial cells (A549): Preventive effect of Pistacia lentiscus essential oil. Toxicol Rep. 2018 Mar 21;5:480-488. doi: 10.1016/j.toxrep.2018.03.012. eCollection 2018. PubMed PMID: 29854619; PubMed Central PMCID: PMC5977410. 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. 11: da Trindade R, da Silva JK, Setzer WN. Copaifera of the Neotropics: A Review of the Phytochemistry and Pharmacology. Int J Mol Sci. 2018 May 18;19(5). pii: E1511. doi: 10.3390/ijms19051511. Review. PubMed PMID: 29783680; PubMed Central PMCID: PMC5983702. 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.