29106-32-9

Basic information

• Product Name: CHAULMOOGRIC ACID
• Synonyms: (s)-2-cyclopentene-1-tridecanoicaci;(s)-2-cyclopentene-1-tridecanoicacid;26989 AND 52425;2-Cyclopentene-1-tridecanoic acid, (S)-;CHAULMOOGRIC ACID;GYNOCARDIC ACID;13-(cyclopent-2-enyl)tridecanoic acid;2-cyclopentene-1-undecanoic acid
• CAS NO: 29106-32-9
• Molecular Formula: C₁₈H₃₂O₂
• Molecular Weight: 280.45
• EINECS: 249-440-7
• Mol File: 29106-32-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 68.5°
• Boiling Point: bp20 247-248°
• Flash Point: 305°C
• Appearance: /
• Density: 0.9504 (rough estimate)
• Vapor Pressure: 8.29E-08mmHg at 25°C
• Refractive Index: 1.5510 (estimate)
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: CHAULMOOGRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CHAULMOOGRIC ACID(29106-32-9)
• EPA Substance Registry System: CHAULMOOGRIC ACID(29106-32-9)

Safety Data

• Hazardous Substances Data: 29106-32-9(Hazardous Substances Data)

Usage

Uses

Chaulmoogric Acid is a component of chaulmoogra oil and used to treat leprosy.

Purification Methods

Crystallise the acid from pet ether or EtOH. The Me ester [24828-59-9] has m 22o, b 227o/20mm and [ ] D 15 +50o (c 5, CHCl3). [Mislow & Steinberg J Am Chem Soc 77 3807 1955.]

InChI:InChI=1/C18H32O2/c19-18(20)16-10-8-6-4-2-1-3-5-7-9-13-17-14-11-12-15-17/h11,14,17H,1-10,12-13,15-16H2,(H,19,20)/t17-/m1/s1

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Relevant articles and documents

Syntheses of enantiomerically pure cyclopent-2-ene-1-carboxylic acid and (cyclopent-2-enyl)acetic acid by enantioselective palladium-catalyzed allylic alkylations - Synthesis of enantiomerically pure (-)-chaulmoogric acid

Asymmetric Pd-catalyzed allylic alkylations of dimethyl malonate and diethyl 2-acetoxymalonate with 3-chlorocyclopentene, using phosphanyloxazolines 1 and ent-1 as chiral ligands, gave products (-)-2 and (+)-3b with 95 and 99.5% ee, respectively. Oxidative degradation of (+)-3b furnished (+)-(R)-cyclopent-2-ene-1-carboxylic acid [(+)-4] with > 99% ee. Alkylation product (-)-2 was transformed into enantiomerically pure (-)-(R)-(cyclopent-2-enyl)acetic acid [(-)-5] by three simple steps. Availability of (-)-5 enabled the first synthesis of enantiomerically pure (-)-chaulmoogric acid [(-)-9] in three steps. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.