(-)-trans-Caryophyllene - ≥98% , CAS No.87-44-5

CAS: 87-44-5 Cat. No.: T334030 Molecular Weight: 204.35 Beilstein Registry Number: 2044564 EC Number: 201-746-1

GRADE & PURITY ≥98%

Synonyms

(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene | (-)-E-Caryophyllene | .beta.-Caryophyllen | 1-CARYOPHYLLENE | CHEBI:10357 | FEMA No. 2252 | MFCD00075925 | (E)-Caryophyllene | P198906 | BETA-CARYOPHYLLENE [INCI]

Storage

Room temperature

Shipped In

Normal

Overview

(-)-trans-Caryophyllene, a sesquiterpene, is the major constituent in the essential oil of Mentha longifolia and Commiphora gileadensis. It shows anti-inflammatory, local anaesthetic and antifungal properties. (-)-trans-Caryophyllene also shows potent cytotoxic activity. 

Specifications

Synonyms

(1R, 4E, 9S)-4, 11, 11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene | (-)-E-Caryophyllene | .beta.-Caryophyllen | 1-CARYOPHYLLENE | CHEBI:10357 | FEMA No. 2252 | MFCD00075925 | (E)-Caryophyllene | P198906 | BETA-CARYOPHYLLENE [INCI]

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488195238
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195238
• Canonical Smiles: CC1=CCCC(=C)C2CC(C2CC1)(C)C
• IUPAC Name: (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
• InChIKey: NPNUFJAVOOONJE-GFUGXAQUSA-N
• 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
• Isomeric SMILES: C/C/1=C\CCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
• WGK Germany: 1
• RTECS: DT8400000
• Molecular Weight: 204.35
• Beilstein: 2044564

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Sesquiterpenoids
• Alternative Parents: Polycyclic hydrocarbons Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Caryophyllane sesquiterpenoid - Sesquiterpenoid - Branched unsaturated hydrocarbon - Polycyclic hydrocarbon - Cyclic olefin - Unsaturated aliphatic hydrocarbon - Unsaturated hydrocarbon - Olefin - Hydrocarbon - Aliphatic homopolycyclic compound
• Description: 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

Associated Targets(Human)

PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)

Discover Target: PPARA

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CNR2 Tchem Cannabinoid CB2 receptor (16942 Activities)

Discover Target: CNR2

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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Pseudomonas aeruginosa (123386 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Cutibacterium acnes (887 Activities)

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Trypanosoma cruzi (99888 Activities)

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Meloidogyne incognita (862 Activities)

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Mus musculus (284745 Activities)

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Tetranychus urticae (2600 Activities)

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LLC-MK2 (227 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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dengue virus type 2 (2400 Activities)

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Ileum (29 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ether, chloroform, alcohol, and ethyl acetate. Insoluble in water.
• Refractive Index: n20D1.50
• Specific Rotation[α]: -9.2°
• Flash Point(°C): 97 °C
• Boil Point(°C): 262-264° C
• Molecular Weight: 204.350 g/mol
• XLogP3: 4.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.188 Da
• Monoisotopic Mass: 204.188 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 293.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Wen Zhang, Xu-Dong Wang, Xiao-Han Zhang, Rui Feng, Jun-Long Wang, Wei-Bao Kong, Ji Zhang, Jun-Yu Liang.  (2023)  Biological activities of Elsholtzia stauntoni essential oil and its major constituents against Tribolium castaneum larvae and Lasioderma serricorne adults.  Journal of Essential Oil Bearing Plants,      [PMID:] [10.1080/0972060X.2023.2273262]

2. Jiang Zheng, Zhou Peina, Shao Yongfang, Zhang Qianqian, Yue Wei, Qu Cheng, Wu Qinan.  (2023)  Applying quantitative spatial phenotypes analysis to the investigation of peltate glandular trichomes development pattern in Perilla frutescens.  Plant Methods,  19  (1): (1-17).  [PMID:37626389] [10.1186/s13007-023-01072-4]

3. Surui Lu, Hong Deng, Chenyao Zhou, Zhengda Du, Xuena Guo, Yanfei Cheng, Xiuping He.  (2023)  Enhancement of β-Caryophyllene Biosynthesis in Saccharomyces cerevisiae via Synergistic Evolution of β-Caryophyllene Synthase and Engineering the Chassis.  ACS Synthetic Biology,      [PMID:37224386] [10.1021/acssynbio.3c00024]

4. Jianjun Cheng, Qinghua Chen, Qianshuang Guo, Yongjun Du.  (2022)  Moth sex pheromones affect interspecific competition among sympatric species and possibly population distribution by modulating pre-mating behavior.  Insect Science,  30  (2): (501-516).  [PMID:35900899] [10.1111/1744-7917.13099]

5. Ruijia Liu, Nan Qi, Jie Sun, Haitao Chen, Ning Zhang, Baoguo Sun.  (2022)  Effects of Frying Conditions on Volatile Composition and Odor Characteristics of Fried Pepper (Zanthoxylum bungeanum Maxim.) Oil.  Foods,  11  (11): (1661).  [PMID:35681412] [10.3390/foods11111661]

6. Yuanpeng Hao, Jiamu Kang, Rui Yang, Hui Li, Hongxia Cui, Hongtong Bai, Andrey Tsitsilin, Jingyi Li, Lei Shi.  (2021)  Multidimensional exploration of essential oils generated via eight oregano cultivars: Compositions, chemodiversities, and antibacterial capacities.  FOOD CHEMISTRY,      [PMID:34865929] [10.1016/j.foodchem.2021.131629]

7. Kai Hong, Zhenzhen Xu, Limin Wang, Agbaka Johnpaul, Yongqiang Cheng, Chenyan Lv, Changwei Ma.  (2021)  Varietal differences in the phytochemical components’ accumulation and aroma profile of three Humulus lupulus cultivars.  FOOD CONTROL,      [PMID:] [10.1016/j.foodcont.2021.108499]

8. Hao Dong, Jiapeng He, Kaijun Xiao, Chao Li.  (2019)  Temperature-sensitive polyurethane (TSPU) film incorporated with carvacrol and cinnamyl aldehyde: antimicrobial activity, sustained release kinetics and potential use as food packaging for Cantonese-style moon cake.  INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY,  55  (1): (293-302).  [PMID:] [10.1111/ijfs.14276]

9. Ping Chen, Bing Liu, Xin Liu, Jihong Fu.  (2019)  Ultrasound-assisted extraction and dispersive liquid–liquid microextraction coupled with gas chromatography-mass spectrometry for the sensitive determination of essential oil components in lavender.  Analytical Methods,  11  (11): (1541-1550).  [PMID:] [10.1039/C8AY02687D]

10. Tian Bao-liang, Liu Qi-Zhi, Liu Zhi-Long, Li Peng, Wang Jie-Wen.  (2015)  Insecticidal Potential of Clove Essential Oil and Its Constituents on Cacopsylla chinensis (Hemiptera: Psyllidae) in Laboratory and Field.  JOURNAL OF ECONOMIC ENTOMOLOGY,  108  (3): (957-961).  [PMID:26470216] [10.1093/jee/tov075]

11. Xiaoming Zeng, Hao He, Liejiang Yuan, Haizhi Wu, Cong Zhou.  (2024)  Determination of 24 Trace Aromatic Substances in Rosemary Hydrosol by Dispersed Liquid–Liquid Microextraction–Gas Chromatography.  Processes,  12  (3): (498).  [PMID:] [10.3390/pr12030498]

12. Haoran Pei, Gang Xie, Xiang Yao, Shenghui Wang, Jin Yan, Liangying Dai, Yunsheng Wang.  (2024)  Exploring the binding affinity and characteristics of DcitOBP9 in citrus psyllids.  GENE,      [PMID:38759737] [10.1016/j.gene.2024.148551]

13. Yuwen Chen, Zhishuang Zhu, Weikai Yang, Yu Zhang, Jiawei Yang, Liulian Huang, Huichao Hu, Jianguo Li, Lihui Chen.  (2024)  Investigating the emission of volatile organic compound from Cinnamomum camphora.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2024.119134]

14. Suqi Liu, Linjiang Pang, Xiaowei Wu, Shihao Chen, Mingyi Yang, Jiyu Cheng, Guoquan Lu, Zhenhe Wang, Wei Chen, Yuge Guan, Xinghua Lu.  (2024)  Non-destructive detection of trans-caryophyllene in early sweetpotato black spot disease using a QCM gas sensor based on modified CAU-1@ZIF-8 composite.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.110782]

15. Suqi Liu, Xiaowei Wu, Shihao Chen, Cong Liu, Wanqi Zhang, Mingyi Yang, Jiyu Cheng, Guoquan Lu, Zhenhe Wang, Wei Chen, Yuge Guan, Linjiang Pang, Xinghua Lu.  (2025)  Rapid detection of linalool by QCM gas sensor based on HKUST-1/MWCNT-gel@MIP in early sweetpotato black spot disease.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.113232]

16. Li Zhang, Hui Wu, Xiaoyuan Li, Xiu Zhang, Hua Li, Huaqiao Tang, Daxuan Tang, Shijing Du, Ya’’ou Liu, Yangfan Tang, Xiaoming Bao, Guoqiang Cheng.  (2025)  Screening bioactive compounds from Qianghuo (Notopterygium incisum) volatile oil via COX-2 magnetic ligand fishing.  FITOTERAPIA,      [PMID:39955008] [10.1016/j.fitote.2025.106432]

17. Huijuan Zhang, Jiefen Cui, Guifang Tian, Christina DiMarco-Crook, Wei Gao, Chengying Zhao, Genyuan Li, Yunhe Lian, Hang Xiao, Jinkai Zheng.  (2019)  Efficiency of four different dietary preparation methods in extracting functional compounds from dried tangerine peel.  FOOD CHEMISTRY,      [PMID:30955622] [10.1016/j.foodchem.2019.03.063]

18. Deng Jie, Zheng Jia, Li Xing, Huang Dan, Ye Guangbin, Luo Huibo.  (2025)  Characterization of Qu-aroma of medium–high temperature Daqu from different production areas using sensory evaluation, E-nose, and GC–MS/O analysis.  Bioresources and Bioprocessing,  12  (1): (1-16).  [PMID:40285888] [10.1186/s40643-025-00863-y]

19. Yapeng Zhang, Chenwen Liu, Wenqiang Li, Zhidong Ma, Bo Lv, Lei Qin, Chun Li.  (2025)  Systematic engineering of the sterol synthesis pathway for Saccharomyces cerevisiae promotes the efficient production of β-caryophyllene.  METABOLIC ENGINEERING,      [PMID:40480515] [10.1016/j.ymben.2025.06.004]

20. Jing Ma, Dengyu Li, Mengdie Xu, Yimeng Xia, Gaowei Fang, Qiuhui Wei, Xiaoxia Ma, Yifeng Zhang, Qin Zhang, Yuhan Hu, Jiawei Zhou, Xiaopu Yin, Tianyuan Hu.  (2025)  Multifunctional sesquiterpene synthase from Curcuma wenyujin reveals the biosynthetic mechanism of sesquiterpenes with diverse skeletons.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40505938] [10.1016/j.ijbiomac.2025.145152]

21. Mengdie Xu, Yimeng Xia, Gaowei Fang, Tangli Li, Jing Ma, Dengyu Li, Qiuhui Wei, Lichan Tu, Xiaopu Yin, Tianyuan Hu.  (2025)  Characterization of a sesquiterpene synthase and a short-chain dehydrogenase in zerumbone biosynthesis and the applications in engineered Saccharomyces cerevisiae.  Frontiers in Plant Science,      [PMID:41114138] [10.3389/fpls.2025.1635141]

22. Xu Xu, Sheng-Dong Wang, Li-Ping Liu, Qiang Fu, Jun Zheng, Ling-Ling Lyu.  (2025)  Screening of Active Component form Essential Oil and Investigation of Its Synergistic Enhancement on the Mosquito-Repellent Efficacy of p-Menthane-3,8-diol.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41428740] [10.1021/acs.jafc.5c08671]

23. Christian Neckie Natt, Chaoqun Yi, Longfei Shi, Ruonan Li, Adel Khashaveh, Wentao Liu, Yongjun Zhang.  (2025)  Plant volatiles drive Spodoptera frugiperda behavioral preference to sweet corn.  Frontiers in Ecology and Evolution,      [PMID:] [10.3389/fevo.2025.1729374]

24. Jiarui Tong, Xiangrong Zhu, Xiumei Chen, Nengguo Tao.  (2026)  Trans-2-hexenal-loaded gelatin/dialdehyde starch/nanocellulose cushioning aerogel: synergistic postharvest preservation of Chinese bayberry with 1-MCP.  FOOD RESEARCH INTERNATIONAL,      [PMID:41794491] [10.1016/j.foodres.2026.118612]

25. Ying Wang, Yi-Tong Du, Wen-bo Yan, Zi-Tao Jiang, Jin Tan.  (2026)  A fast and simple flow injection chemiluminescence method to evaluate antioxidant and free radical scavenging abilities of essential oils.  JOURNAL OF ESSENTIAL OIL RESEARCH,      [PMID:] [10.1080/10412905.2026.2631072]

26. Wang Lei, Hu Hanlu, Sun Xiaoxia, Jiao Ziwei, Zhang Hao, Luo Weikang, Huang Xiaode.  (2026)  Exploring the antibacterial mechanism and application of lavender essential oil based on network pharmacology and molecular docking.  Scientific Reports,      [PMID:] [10.1038/s41598-026-52170-x]