Patchouli alcohol - 10mM in DMSO , CAS No.5986-55-0

CAS: 5986-55-0 Cat. No.: P424979 Molecular Weight: 222.37 EC Number: 227-807-2

GRADE & PURITY 10mM in DMSO

Synonyms

(-)-(1R,3R,6S,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.0(3,8)]undecan-3-ol | PATCHOULI ALCOHOL [MI] | CCG-266740 | Patchoulic alcohol | DTXSID9052266 | Healingwood | octahydro-4,8a,9,9-tetramethyl- | patchoulanol | Patchoulol | (-)-patchouli alcohol | 1,6

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

(-)-(1R, 3R, 6S, 7S, 8S)-2, 2, 6, 8-tetramethyltricyclo[5.3.1.0(3, 8)]undecan-3-ol | PATCHOULI ALCOHOL [MI] | CCG-266740 | Patchoulic alcohol | DTXSID9052266 | Healingwood | octahydro-4, 8a, 9, 9-tetramethyl- | patchoulanol | Patchoulol | (-)-patchouli alcohol | 1, 6

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Pubchem Sid: 528773703
• Canonical Smiles: CC1CCC2(C(C3CCC2(C1C3)C)(C)C)O
• IUPAC Name: (1R,3R,6S,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol
• InChIKey: GGHMUJBZYLPWFD-CUZKYEQNSA-N
• INCHI: 1S/C15H26O/c1-10-5-8-15(16)13(2,3)11-6-7-14(15,4)12(10)9-11/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m0/s1
• Isomeric SMILES: C[C@H]1CC[C@@]2([C@@]3([C@H]1C[C@H](C2(C)C)CC3)C)O
• Molecular Weight: 222.37
• Reaxy-Rn: 2500518
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2500518&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Alcohols and polyols

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Not available
• Direct Parent: Tertiary alcohols
• Alternative Parents: Cyclic alcohols and derivatives Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Tertiary alcohol - Cyclic alcohol - Hydrocarbon derivative - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as tertiary alcohols. These are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
• External Descriptors: tertiary alcohol - sesquiterpenoid - carbotricyclic compound

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)

HEK293 (82097 Activities)

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Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 222.370 g/mol
• XLogP3: 4.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 222.198 Da
• Monoisotopic Mass: 222.198 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 321.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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. Qian-Qian Peng, Qi Guo, Cheng Chen, Ping Song, Yue-Tong Wang, Xiao-Jun Ji, Chao Ye, Tian-Qiong Shi.  (2023)  High-Level Production of Patchoulol in Yarrowia lipolytica via Systematic Engineering Strategies.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:36883816] [10.1021/acs.jafc.3c00222]

2. Guangjuan Luo, Ying Lin, Shuting Chen, Ruiming Xiao, Jiaxin Zhang, Cheng Li, Anthony J. Sinskey, Lei Ye, Shuli Liang.  (2023)  Overproduction of Patchoulol in Metabolically Engineered Komagataella phaffii.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:36681940] [10.1021/acs.jafc.2c08228]

3. Fu Xueqing, Zhang Fangyuan, Ma Yanan, Hassani Danial, Peng Bowen, Pan Qifang, Zhang Yuhua, Deng Zhongxiang, Liu Wenbo, Zhang Jixiu, Han Lei, Chen Dongfang, Zhao Jingya, Li Ling, Sun Xiaofen, Tang Kexuan.  (2021)  High-Level Patchoulol Biosynthesis in Artemisia annua L..  Frontiers in Bioengineering and Biotechnology,      [PMID:33614607] [10.3389/fbioe.2020.621127]

4. Min Liu, Yang-Chen Lin, Jiao-Jiao Guo, Meng-Meng Du, Xinyi Tao, Bei Gao, Ming Zhao, Yushu Ma, Feng-Qing Wang, Dong-Zhi Wei.  (2021)  High-Level Production of Sesquiterpene Patchoulol in Saccharomyces cerevisiae.  ACS Synthetic Biology,      [PMID:33395273] [10.1021/acssynbio.0c00521]

5. Basharat Mehmood, Mohammad Akbar, Rahmat Ullah.  (2020)  Accelerated aging effect on high temperature vulcanized silicone rubber composites under DC voltage with controlled environmental conditions.  ENGINEERING FAILURE ANALYSIS,      [PMID:] [10.1016/j.engfailanal.2020.104870]

6. Bin Ma, Min Liu, Zhen-Hai Li, Xinyi Tao, Dong-Zhi Wei, Feng-Qing Wang.  (2019)  Significantly Enhanced Production of Patchoulol in Metabolically Engineered Saccharomyces cerevisiae.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:31287301] [10.1021/acs.jafc.9b03456]

7. Jun-Feng Wang, Xiao-Lan Wang.  (2013)  Thermochemical properties of two mixed alkali-alkaline earth metal borates as non-linear optical materials: NaSrBO3 and KSr4B3O9.  JOURNAL OF CHEMICAL THERMODYNAMICS,      [PMID:] [10.1016/j.jct.2013.11.033]

8. Guangjuan Luo, Ying Lin, Shupeng Ruan, Ruiming Xiao, Xinying Zhang, Shuli Liang.  (2024)  Dual cytoplasmic-mitochondrial engineering for improved patchoulol production in Komagataella phaffii.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2024.109286]

9. Mingyu Dai, Qingyi Cao, Shuanglong Jia, Jiang Chen, Hui-Ying Xu, Bang-Ce Ye, Wei-Bing Liu, Ying Zhou.  (2025)  Engineering Yarrowia lipolytica for High-Level β-elemene Production via Combinatorial Metabolic Strategies.  Synthetic and Systems Biotechnology,      [PMID:40689232] [10.1016/j.synbio.2025.06.007]

10. Xiaochun Zheng, Yajun Li, Zhenhua Liu, Peng Sun, Yaqi Dong, Xue Wang, Yanan Wang, Xiaobing Yang.  (2026)  Biosynthesis of patchoulol via metabolic engineering the oleaginous red yeast Rhodotorula toruloides.  Synthetic and Systems Biotechnology,      [PMID:41551742] [10.1016/j.synbio.2025.12.003]

11. Li Li, Yasen Wang, Buqing Wang, Liqun Shen, Yahui Gao, Wei Lin, Zijie Li.  (2026)  A dCas9-integrated iLight9O system enables dynamic regulation for enhanced patchoulol biosynthesis in Saccharomyces cerevisiae.  BIORESOURCE TECHNOLOGY,      [PMID:41679604] [10.1016/j.biortech.2026.134195]