6-(benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid

• ChemBase ID: 92165
• Molecular Formular: C17H15NO4
• Molecular Mass: 297.3053
• Monoisotopic Mass: 297.10010797
• SMILES: [nH]1c2c(cc(c(c2)OCc2ccccc2)OC)cc1C(=O)O
• Canonical SMILES: COc1cc2cc([nH]c2cc1OCc1ccccc1)C(=O)O
• InChI: InChI=1S/C17H15NO4/c1-21-15-8-12-7-14(17(19)20)18-13(12)9-16(15)22-10-11-5-3-2-4-6-11/h2-9,18H,10H2,1H3,(H,19,20)
• InChIKey: JMOOGCFXFNKYCS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid
• IUPAC Traditional name: 6-(benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid
• Synonyms: NSC 92530; 6-Benzyloxy-5-methoxy-2-carboxyindole; 5-Methoxy-6-(phenylmethoxy)-1H-indole-2-carboxylic Acid; 6-Benzyloxy-5-methoxyindole-2-carboxylic acid; 6-苄氧基-5-甲氧基-2-羧基吲哚

Database IDs

• CAS Number: 2495-92-3
• MDL Number: MFCD00055977
• PubChem SID: 24891571; 162078863
• PubChem CID: 260801

CALCULATED PROPERTIES

• Acid pKa: 3.6033747
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.1666203
• LogD (pH = 7.4): -0.2831353
• Log P: 3.0587225
• Molar Refractivity: 81.8172 cm^3
• Polarizability: 32.487427 Å^3
• Polar Surface Area: 71.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Clear Yellow Solution in Pyridine @ 50mg/ml.
• Apperance: Tan Crystals; tan powder
• Melting Point: 230-232(dec.)°C; 230-232°C dec.

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... SRD5A1(6715), SRD5A2(6716)

Product Information

• Purity: ≥99%

DETAILS

Sigma Aldrich - B1251

包装
500 mg in poly bottle
Application

• Reactant for preparation of indolecarboxamides with antitumor activity in human lung cancer1
• Reactant for preparation of benzophenone- and indolecarboxylic acids as potent type-2 specific inhibitors of human steroid 5α-reductase2

REFERENCES

• J. Heterocyclic Chem., 2, 387 (1965)