(-)-Perillaldehyde - ≥90%(GC) , CAS No.18031-40-8

CAS: 18031-40-8 Cat. No.: P160187 Formula: C₁₀H₁₄O Molecular Weight: 150.22 Beilstein Registry Number: 2326450 EC Number: 679-812-8 PubChem CID: 2724159

GRADE & PURITY ≥90%(GC)

Synonyms

(4S)-perillyl aldehyde | DTXCID3021190 | DS-4065 | RUMOYJJNUMEFDD-SNVBAGLBSA-N | (4S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde | (4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde | 1-Perillaldehyde | 4-Isopropenyl-1-cyclohexene-1-carbaldehyde, (S)

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

(S)-(-)-Perillaldehyde is a monoterpene aldehyde mainly found in the herb, Perilla frutescens.It is the key volatile flavor compound of orange juice and mandarin peel oil.

Specifications

Synonyms

(4S)-perillyl aldehyde | DTXCID3021190 | DS-4065 | RUMOYJJNUMEFDD-SNVBAGLBSA-N | (4S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde | (4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde | 1-Perillaldehyde | 4-Isopropenyl-1-cyclohexene-1-carbaldehyde, (S)

Specifications & Purity

≥90%(GC)

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥90%(GC)

Names and Identifiers

• Pubchem Sid: 504760857
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760857
• Canonical Smiles: CC(=C)C1CCC(=CC1)C=O
• IUPAC Name: (4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde
• InChIKey: RUMOYJJNUMEFDD-SNVBAGLBSA-N
• INCHI: 1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m1/s1
• Isomeric SMILES: CC(=C)[C@H]1CCC(=CC1)C=O
• WGK Germany: 3
• RTECS: GW2967200
• PubChem CID: 2724159
• Molecular Weight: 150.22
• Beilstein: 2326450
• Reaxy-Rn: 4662920

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Menthane monoterpenoids
• Alternative Parents: Monocyclic monoterpenoids Organic oxides Hydrocarbon derivatives Aldehydes
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: P-menthane monoterpenoid - Monocyclic monoterpenoid - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aldehyde - Aliphatic homomonocyclic compound
• Description: 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: p-menthane monoterpenoid

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light & air sensitive
• Refractive Index: 1.51
• Specific Rotation[α]: [α]20/D −120°, c = 10 in ethanol
• Flash Point(°F): 204.8 °F
• Flash Point(°C): 96 °C
• Boil Point(°C): 98°C/7mmHg
• Molecular Weight: 150.220 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• 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: 201.000
• 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

References

1. Xiuling Meng, Weijie Wu, Ben Niu, Ruiling Liu, Huizhi Chen, Haiyan Gao, Hangjun Chen.  (2023)  Inhibitory effect and action mechanism of perillaldehyde on the Fusarium graminearum in postharvest fresh ginger.  POSTHARVEST BIOLOGY AND TECHNOLOGY,      [PMID:] [10.1016/j.postharvbio.2023.112674]

2. Zhu Ji-Xiao, Hu Wei-Qiong, Dong Shu-Qi, Yi Li-Tao, Zeng Jin-Xiang, Li Min.  (2019)  Hippocampal BDNF signaling is required for the antidepressant effects of perillaldehyde.  Pharmacological Reports,  71  (3): (430-437).  [PMID:31003153] [10.1016/j.pharep.2019.01.009]

3. Ma Wei-Bin, Feng Jun-Tao, Jiang Zhi-Li, Wu Hua, Ma Zhi-Qing, Zhang Xing.  (2014)  Fumigant activity of eleven essential oil compounds and their selected binary mixtures against Culex pipiens pallens (Diptera: Culicidae).  PARASITOLOGY RESEARCH,  113  (10): (3631-3637).  [PMID:25015050] [10.1007/s00436-014-4028-0]

4. Ji Liu, Ying Han, Zhiyun Wu, Manli Chen, Wenwen Wu, Zijun Zhao, Jinjin Yuan, Zhijian Zheng, Qiang Lin, Nan Liu, Hongbin Chen.  (2024)  Perillaldehyde pretreatment alleviates cerebral ischemia-reperfusion injury by improving mitochondrial structure and function via the Nrf2/Keap1/Trx2 axis.  PHYTOMEDICINE,      [PMID:39765034] [10.1016/j.phymed.2024.156328]

5. Mohammed Mustafa Yousif Modwi, Yafei Liu, Fuyuan Li, Ying Lv, Abdalbagi Ismail, Dafaalla Hassan, Huixia Feng.  (2025)  Theoretical and Experimental Investigation of Chitosan/Perillaldehyde Schiff Base as a Corrosion Inhibitor for Q235 Carbon Steel in Acidic Medium.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2025.142001]

6. Shuqi Liu, Yuxin Jiang, Jiancheng Sun, Fan Yang, Yuqing Wang, Yongqing Lu, Weiqiang Lai, Chao-an Long.  (2025)  Perillaldehyde controls citrus green mold by inhibiting the ribosome biogenesis of Penicillium digitatum and improving citrus disease resistance.  FOOD CONTROL,      [PMID:] [10.1016/j.foodcont.2025.111595]

7. Mohammed Mustafa Yousif Modwi, Huixia Feng, Yafei Liu, Fuyuan Li, Juanjuan Zhao.  (2025)  Study on synthesized corrosion inhibitor of chitosan and menthone based on Schiff base for carbon steel in the acidic environment.  Journal of the Taiwan Institute of Chemical Engineers,      [PMID:] [10.1016/j.jtice.2025.106322]

8. Yunpeng Hao, Qihang Chen, Meiling Liu, Yankun Yang, Xiuxia Liu, Chun-Li Liu, Zhonghu Bai.  (2026)  Engineering a Substrate-Affinitive and Thermostable YqhD Variant for Efficient Bioconversion of Perillyl Aldehyde to Perillyl Alcohol.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41504486] [10.1021/acs.jafc.5c09114]

9. Qing Chen, Sitian Wang, Jiarui Jiang, Lianwen Hu, Fuge Niu, Weichun Pan, Yanbo Wang, Xiaoxiang Han.  (2026)  Carboxymethyl chitosan perilla essential oil Schiff base as promising antibacterial agent: preparation, characterization, and activity.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:41692199] [10.1016/j.ijbiomac.2026.150935]

10. Yong-xin Li, Chao Pan, Yuting Sun, Zihan Zhou, Yuanhang Ni, Kunlong Yang, Ling Shen, Jun Tian.  (2026)  Nitrogen-responsive regulators AfnirA and AfcrnA differentially affect oxidative stress adaptation and aflatoxin biosynthesis in Aspergillus flavus.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2026.109526]