4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

• ChemBase ID: 6015
• Molecular Formular: C14H12O4
• Molecular Mass: 244.24268
• Monoisotopic Mass: 244.07355886
• SMILES: c1(cc(cc(c1)/C=C/c1cc(c(cc1)O)O)O)O
• Canonical SMILES: Oc1cc(/C=C/c2ccc(c(c2)O)O)cc(c1)O
• InChI: InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+
• InChIKey: CDRPUGZCRXZLFL-OWOJBTEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol; 5-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol
• IUPAC Traditional name: 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol; piceatannol
• Synonyms: 4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol; (E)-3,3',4,5'-Stilbenetetrol; Piceatannol; Astringenin; trans-3,3',4,5'-Tetrahydroxystilbene; (E)-Piceatannol; trans-Piceatannol; 3',4',3,5-tetrahydroxy-trans-stilbene; Astringinin; (E)-4-[2-(3,5Dihydroxyphenyl)ethenyl]1,2-benzenediol; 3,3′,4,5′-Tetrahydroxy-trans-stilbene; Piceatannol; PICEATANNOL; 3,3',4,5'-Tetrahydroxystilbene

Database IDs

• CAS Number: 10083-24-6
• MDL Number: MFCD00221715
• PubChem SID: 24278620; 99444870; 160969440
• PubChem CID: 667639
• Chemspider ID: 581006
• Wikipedia Title: Piceatannol

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.905793
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 3.098656
• LogD (pH = 7.4): 3.0854614
• Log P: 3.0988255
• Molar Refractivity: 69.4364 cm^3
• Polarizability: 25.926823 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.12
• LOG S: -3.4
• Solubility (Water): 9.70e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mg/mL; ethanol: soluble10 mg/mL; H2O: soluble0.5 mg/mL
• Apperance: Light tan to yellow powder; light tan to yellow powder; Powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Gene Information: human ... CDK2(1017)

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB08399

Drug information: experimental

Sigma Aldrich - P0453

Biochem/physiol Actions
A plant metabolite possessing anti-leukemic activity; inhibits the non-receptor kinases, Syk and Lck.
Physical form
Photosensitive powder
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P0453.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P436300

A human metabolite of Resveratrol (R150000).

REFERENCES

• Athar, M., et al.: Toxicol. Appl. Pharmacol., 224, 274 (2007)
• Bernhardt, R., et al.: J. Biotechnol., 124, 128 (2007)
• Fairman, D.A., et al.: Drug Metab. Dispos., 35, 2159 (2007)