Pinosylvin - ≥97%(HPLC) , CAS No.22139-77-1

CAS: 22139-77-1 Cat. No.: P168709 Molecular Weight: 212.24 EC Number: 683-184-0 PubChem CID: 5280457

GRADE & PURITY ≥97%(HPLC)

Synonyms

5-(2-phenylethenyl)-1,3-benzenediol | Stilbene, 3,5-dihydroxy-, trans- | BCP18617 | Stilbene, 1f | 5-[(1E)-2-phenylethenyl]-1,3-benzenediol | PINOSYLVIN [MI] | Q7196412 | AS-76520 | DTXSID00895857 | 1,3-Benzenediol, 5-(2-phenylethenyl)-, (E)- | NSC 36243

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

application：

Pinosylvin, a pre-infectious stilbenoid toxin, is used to study its properties as a fungitoxin and therapeutic agent. Pinosylvin is used as a representative stilbene to study its biological actions and therapeutic value in processes such as cell survival, apoptosis and cell mobility.

Specifications

Synonyms

5-(2-phenylethenyl)-1, 3-benzenediol | Stilbene, 3, 5-dihydroxy-, trans- | BCP18617 | Stilbene, 1f | 5-[(1E)-2-phenylethenyl]-1, 3-benzenediol | PINOSYLVIN [MI] | Q7196412 | AS-76520 | DTXSID00895857 | 1, 3-Benzenediol, 5-(2-phenylethenyl)-, (E)- | NSC 36243

Specifications & Purity

≥97%(HPLC)

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Purity

≥97%(HPLC)

Names and Identifiers

• Pubchem Sid: 504763302
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763302
• Canonical Smiles: C1=CC=C(C=C1)C=CC2=CC(=CC(=C2)O)O
• IUPAC Name: 5-[(E)-2-phenylethenyl]benzene-1,3-diol
• InChIKey: YCVPRTHEGLPYPB-VOTSOKGWSA-N
• INCHI: 1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O
• PubChem CID: 5280457
• Molecular Weight: 212.24

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Stilbenes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Styrenes Resorcinols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Stilbene - Styrene - Resorcinol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
• External Descriptors: Diphenyl ethers, biphenyls, dibenzyls and stilbenes

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)

LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

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TRPV1 Tclin Vanilloid receptor (8273 Activities)

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HL-60 (67320 Activities)

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

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

Discover Target: SLCO1B3

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Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)

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Mus musculus (284745 Activities)

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Botrytis cinerea (4183 Activities)

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RAW264.7 (28094 Activities)

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J774 (3120 Activities)

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B16-F10 (4610 Activities)

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Nqo1 NAD(P)H dehydrogenase [quinone] 1 (1058 Activities)

Discover Target: Nqo1

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

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Cladosporium herbarum (157 Activities)

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Diaporthe ampelina (88 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Sensitivity: light & air sensitive
• Flash Point(°C): 154-155ºC
• Molecular Weight: 212.240 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 212.084 Da
• Monoisotopic Mass: 212.084 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 221.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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. Ming Su, Lei Ye, Yunbing Tang, Shaowei Wang, Zhiyan Hu, Huitao Li, Yiyan Wang, Xiaoheng Li, Yi Liu, Ren-Shan Ge.  (2023)  Inhibition of Resveratrol Analogs on Human and Rat 3β-Hydroxysteroid Dehydrogenases: Structure–Activity Relationship and Docking Analysis.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:37129992] [10.1021/acs.jafc.3c01919]

2. C. Hu, Y. Zhai, H. Lin, H. Lu, J. Zheng, C. Wen, X. Li, R.S. Ge, Y. Liu, Q. Zhu.  (2024)  Resveratrol analogues and metabolites selectively inhibit human and rat 11β-hydroxysteroid dehydrogenase 1 as the therapeutic drugs: structure–activity relationship and molecular dynamics analysis.  SAR AND QSAR IN ENVIRONMENTAL RESEARCH,      [PMID:39139138] [10.1080/1062936X.2024.2389817]

3. Yaxuan Yue, Jing Liu, Chen Li, Fengfeng Chen, Cheng Yang, Bingtian Zhao.  (2025)  Pinosylvin and Sanguinarine Combination to Enhance Antifungal Activity against Candida albicans.  JOURNAL OF MICROBIOLOGY AND BIOTECHNOLOGY,      [PMID:40374536] [10.4014/jmb.2412.12055]

4. Wei Zhang, Xiangbing Wu, Wenming Li, Haifeng Zhang, Yijun Wang, Jing Xu, Wenhao Li, Yi Qin, Zebin Wu, Gaoran Ge, Shujun Lv, Lu Mao, Liangliang Wang, Dechun Geng.  (2025)  Pinosylvin Inhibits Inflammatory and Osteoclastogenesis via NLRP3 Inflammasome.  Advanced Science,      [PMID:40492417] [10.1002/advs.202501532]