methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

• ChemBase ID: 105102
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: COC(=O)/C=C/c1c(O)ccc(O)c1
• Canonical SMILES: COC(=O)/C=C/c1cc(O)ccc1O
• InChI: InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3
• InChIKey: BQCNSTFWSKOWMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate; methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate
• IUPAC Traditional name: methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate; methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate
• Synonyms: Erbstatin analog; 2,5-Dihydroxycinnamic acid methyl ester; Methyl 2,5-dihydroxycinnamate; ERBSTATIN ANALOG; 3-(2,5-Dihydroxyphenyl)-2-propenoic Acid Methyl Ester; Methyl 2,5-Dihydroxycinnamate

Database IDs

• CAS Number: 63177-57-1
• MDL Number: MFCD00132932
• PubChem SID: 162092521; 24893707
• PubChem CID: 5353609

CALCULATED PROPERTIES

• Acid pKa: 9.48247
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.908138
• LogD (pH = 7.4): 1.9046254
• Log P: 1.908183
• Molar Refractivity: 51.7908 cm^3
• Polarizability: 19.525108 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble; H2O: insoluble; Methanol; methanol: soluble
• Apperance: Pale Yellow Solid; yellow crystalline
• Melting Point: 178-180°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: >98%; ≥95%

DETAILS

MP Biomedicals - 02158813

Purity: >98%
Erbstatin is a novel inhibitor of the EGF receptor associated tyrosine kinase^1 . It is an unstable compound and is completely inactivated in serum in 30 minutes. Methyl 2,5-dihydroxycinnamate is a stable erbstatin analog retaining activity after a 60 minute incubation. It inhibits EGF receptor associated tyrosine kinase in vitro (IC₅₀ =0.77 μM)^2 . Inhibition is competitive with substrate and noncompetitive with ATP.

Sigma Aldrich - D2667

Biochem/physiol Actions
Inhibitor of EGF receptor-associated tyrosine kinase.
Caution
Photosensitive.
Linkage
Stable analog of erbstatin.

Toronto Research Chemicals - M302700

A stable Erbstatin analogue that inhibits tyrosine kinase. Shown to delay the S-phase induction by epidermal growth factor in quiescent normal rat kidney cells, without affecting the total amount of DNA synthesis.

REFERENCES

• Imoto, M., et al., Biochem. Int. , 15 : 989 (1987).
• Umezawa, K., et al., FEBS Lett. , 260 : 198 (1990).
• Zheng, J., et al.: Br. J. Pharmacol., 130, 1115 (2000)
• Zhou, G., et al.: J. Clin. Invest., 108, 1167 (2000)
• Reznick, R., et al.: J. Physiol., 574, 33 (2000)