738-87-4

Basic information

• Product Name: Sterculic acid
• Synonyms: 8-(2-Octacyclopropen-1-yl)octanoic acid;8-(2 OCTYL 1-CYCLOPROPENYL) OCTANOIC ACID;STERCULIC ACID;9,10-Methylene-9-octadecenoicacid;2-Octyl-1-cyclopropene-1-octanoic acid;Sterculinic acid;8-(2-octylcyclopropen-1-yl)caprylic acid;8-(2-octylcyclopropen-1-yl)octanoic acid
• CAS NO: 738-87-4
• Molecular Formula: C₁₉H₃₄O₂
• Molecular Weight: 294.47
• Mol File: 738-87-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 19 °C
• Boiling Point: 418.7 °C at 760 mmHg
• Flash Point: 315.4 °C
• Appearance: /
• Density: 0.948 g/cm³
• Vapor Pressure: 3.49E-08mmHg at 25°C
• Refractive Index: 1.486
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: Sterculic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Sterculic acid(738-87-4)
• EPA Substance Registry System: Sterculic acid(738-87-4)

Safety Data

• Hazardous Substances Data: 738-87-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A long-chain, monounsaturated fatty acid composed of 9-octadecenoic acid having a 9,10-cyclopropenyl group.

InChI:InChI=1/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21)

Synthetic route

sodium cyanide (143-33-9) + 1-(7-Iodo-heptyl)-2-octyl-cyclopropene (152389-88-3) → sterculic acid (738-87-4)

Conditions	Yield
With sodium hydroxide

1,ω-diiodoheptane (51526-03-5) → sterculic acid (738-87-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: butyl lithium, HMPA / Ambient temperature 2: aq. NaOH View Scheme

1,1,2-tribromo-2-n-octylcyclopropane (108176-04-1) → sterculic acid (738-87-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: butyl lithium, HMPA / Ambient temperature 2: aq. NaOH View Scheme

sterculic acid (738-87-4) → cis-8-(2-octylcyclopropyl)octanoic acid (4675-61-0)

Conditions	Yield
With Lindlar's catalyst; ethanol Hydrogenation;

sterculic acid (738-87-4) + methyl iodide (74-88-4) → methyl sterculate (3220-60-8)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In dichloromethane

Upstream product

• 108176-04-1 1,1,2-tribromo-2-n-octylcyclopropane 
• 51526-03-5 1,ω-diiodoheptane 
• 143-33-9 sodium cyanide 
• 152389-88-3 1-(7-Iodo-heptyl)-2-octyl-cyclopropene 

Downstream Products

• 3220-60-8 methyl sterculate 
• 4675-61-0 8-((cis)-2-octylcyclopropyl)octanoic acid 

Relevant articles and documents

A new approach to cyclopropene fatty acids

A series of esters of cyclopropene fatty acids, including sterculic, malvalic and sterculynic acids, has been prepared by alkylation of the corresponding 1-lithiocyclopropenes.