693-72-1

Basic information

• Product Name: TRANS-11-OCTADECENOIC ACID
• Synonyms: DELTA 11 TRANS OCTADECENOIC ACID;11-TRANS-OCTADECENOIC ACID;11-OCTADECENOIC ACID (TRANS);11-OCTADECENOIC ACID;VACCENIC ACID (TRANS);VACCENIC ACID;TRANS-VACCENIC ACID;TRANS-11-OCTADECENOIC ACID
• CAS NO: 693-72-1
• Molecular Formula: C₁₈H₃₄O₂
• Molecular Weight: 282.46
• EINECS: 211-758-9
• Product Categories: Dihydro-Flavanols
• Mol File: 693-72-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 44℃
• Boiling Point: 397.91°C (estimate)
• Flash Point: 113 °C
• Appearance: /Liquid
• Density: 0.8563
• Vapor Pressure: 1.81E-06mmHg at 25°C
• Refractive Index: 1.4472 (589.3 nm 50℃)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 4.78±0.10(Predicted)
• Merck: 13,9965
• CAS DataBase Reference: TRANS-11-OCTADECENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-11-OCTADECENOIC ACID(693-72-1)
• EPA Substance Registry System: TRANS-11-OCTADECENOIC ACID(693-72-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• Hazardous Substances Data: 693-72-1(Hazardous Substances Data)

Usage

Uses

Vaccenic Acid is a fatty acid found in Artemia salina that shows antimicrobial activity against a variety of microorganisms except Escherichia coli, Micrococcus luteus and Salmonella enteritidis.

Purification Methods

Crystallise the acid from acetone (m 45-45.5o) or aqueous MeOH (m 43.5-43.7o). The methyl ester has b 174-175o/5mm. [B.eseken & Hoagland Rec Trav Chim, Pays Bas 46 632 1927, Ahmad et al. J Am Chem Soc 70 3391 1948, IR: Rao & Daubert J Am Chem Soc 70 1102 1948.]

InChI:InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h8-9H,2-7,10-17H2,1H3,(H,19,20)/b9-8+

Upstream product

• 506-17-2 cis-vaccenic acid 
• 29780-00-5 methyl 12-tridecenoate 
• 6198-58-9 methyl (Z)-vaccenate 
• 60-33-3 linoleic acid 
• 111-71-7 heptanal 
• 7530-96-3 (11-carboxyundecyl)triphenylphosphonium bromide 
• 1937-63-9 methyl vaccenate 
• 892501-16-5 11-(1-phenyl-1H-tetrazole-5-sulfanyl)undecanoic acid methyl ester 
• 892501-15-4 11-(1-phenyl-1H-tetrazole-5-sulfonyl)undecanoic acid methyl ester 
• 2834-05-1 11-bromoundecanoic acid 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 112-38-9 10-undecenoic acid 
• 112-80-1 cis-Octadecenoic acid 
• 1448529-14-3 C₁₄H₂₅BrO₂ 

Downstream Products

• 339170-22-8 (4R,5S)-4-Methyl-3-((E)-octadec-11-enoyl)-5-phenyl-oxazolidin-2-one 
• 339170-31-9 (4R,5S)-3-((E)-(R)-2-Hydroxy-octadec-11-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 1852-04-6 undecanedioic acid 
• 1937-63-9 methyl vaccenate 

Relevant articles and documents

Nickel-butadiene catalytic system for the cross-coupling of bromoalkanoic acids with alkyl grignard reagents: A practical and versatile method for preparing fatty acids

The knights who say Ni: A practical and convenient synthetic route to fatty acids involves the Ni-catalyzed alkyl-alkyl cross-coupling of bromoalkanoic acids and alkyl Grignard reagents in the presence of 1,3-butadiene as an additive (see scheme). Copyright

Synthesis of trans-vaccenic acid and cis-9-trans-11-conjugated linoleic acid

The preparation of the monounsaturated fatty acid, trans-vaccenic acid 4 (TVA), using both Wittig and one-pot Julia-Kocieński olefination protocol, was achieved in good yield. Similarly a Wittig approach was employed for the stereoselective synthesis of cis-9-trans-11-conjugated linoleic acid 2 from trans-2-nonenal and (8-carboxyoctyl)triphenylphosphonium bromide 12.