cis-9-Octadecenoic acid

• CAS: 112-80-1
• Catalog Number: ACM112801
• Category: Main Products; Fatty Acids and Ester Homologs
• Molecular Weight: 282.50
• Molecular Formula: C18H34O2
• Synonyms: Oleic acid
• IUPAC Name: (Z)-octadec-9-enoicacid
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)O
• InChI Key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N
• Boiling Point: 194-195 °C
• Melting Point: 13-14 °C (lit.)
• Flash Point: 133°F
• Density: 0.89 g/mL at25 °C(lit.)
• Appearance: Viscous Liquid
• Storage: -20°C
• Bond Position Cis Trans: ∆ 9 cis
• CNo.Chain: C18:1
• Compound Derivative: Acid
• EC Number: 204-007-1
• Exact Mass: 282.25600
• Fatty Acid: 9-Octadecenoic; (Oleic)
• Hazard Statements: T,Xi
• Physical State: Viscous Liquid
• Safety Description: 36/37-37/39-26-36-36/37/39
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, aluminium.
• Supplemental Hazard Statements: H320-H319-H315
• Symbol: GHS07
• Type: N9,OMEGA 9
• WGK Germany: 2

Case Study

Synthesis of Estolide Esters from cis-9-Octadecenoic Acid

Harry-O kuru, et al. Journal of the American Oil Chemists' Society, 2001, 78, 219-223.

Cis-9-octadecenoic acid (oleic acid) is first converted into oleic estolide. The obtained oleic estolide can be further esterified with neopentyl alcohol, oleyl alcohol, and 2-propanol to generate the corresponding estolide esters.
Synthesis procedures of estolide esters
· Oleic estolide was synthesized by combining 90% cis-9-octadecenoic acid with 70% perchloric acid in a reaction kettle at 45°C under a nitrogen atmosphere. After 24 hours of stirring, the reaction was quenched with saturated Na2HPO4 and the estolide was separated from the by-product through distillation, yielding 85.1% of the desired product.
· To synthesize 2,2-Dimethyl-1-propyl ester, neopentyl alcohol was reacted with oleic estolide in the presence of toluene and orthophosphoric acid. After reaching 90.7% conversion, the product mixture was purified by washing, drying, and distillation, resulting in a 94% yield of the neopentyl ester.
· Oleyl ester and 2-Propyl ester are also obtained through similar preparation steps, using oleyl alcohol and 2-propanol as raw materials respectively.

Anti-Diarrhoeal Properties of cis-9-Octadecenoic Acid

Garba, S., et al. Org. Med. Chem. IJ, 2017, 3(4), 555619.

One of the most active ingredients available for the treatment of diarrhea has been isolated, extracted and characterized from the Landolphia Owariensis plant. Research has confirmed that the active ingredient compound is cis-9-octadecenoic acid. The compound was found to be highly active against diarrhea-causing microorganisms, suggesting that it could be used as a broad-spectrum antibiotic to treat diarrhea.
Antimicrobial analysis and results
· The cis-9-octadecenoic acid showed varying levels of inhibition zones against Salmonella Typhi, Shigella dysenteriae, and Escherichia coli at concentrations of 2000 µg/cm3, 1000 µg/cm3, 500 µg/cm3, 250 µg/cm3, and 125 µg/cm3.
· At 2000 µg/cm3, the compound had inhibition zones measuring 32 mm, 20 mm, and 25 mm for Salmonella Typhi, Shigella dysenteriae, and Escherichia coli respectively.
· At 1000 µg/cm3, the inhibition zones were 29 mm, 18 mm, and 20 mm for the same bacteria.
Decreasing the concentration to 500 µg/cm3 resulted in inhibition zones of 20 mm, 15 mm, and 17 mm.
· At 250 µg/cm3, the compound had inhibition zones of 20 mm, 10 mm, and 8 mm.
· Finally, at 125 µg/cm3, the compound showed a 15 mm inhibition zone against Salmonella Typhi, but no activity against Shigella dysenteriae and Escherichia coli at that concentration.

Custom Reviews

August 26, 2023

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Multifunctional compound
On the platform, cis-9-octadecenoic acid has many purities and preparations, and has many selectivities.

Custom Q&A

What is the molecular formula of cis-9-octadecenoic acid?

The molecular formula of cis-9-octadecenoic acid is C18H34O2.

What is the molecular weight of cis-9-octadecenoic acid?

The molecular weight of cis-9-octadecenoic acid is 282.46 g/mol.

What is the density of cis-9-octadecenoic acid?

The density of cis-9-octadecenoic acid is 0.895g/ml at 25℃.

What is the character of cis-9-octadecenoic acid?

cis-9-Octadecenoic acid is a colorless or yellowish liquid, with oily taste, insoluble in water, soluble in organic solvents such as ethanol, ether and chloroform.

What's the use of cis-9-octadecenoic acid?

cis-9-Octadecenoic acid can be used to make soap, detergent, lubricating oil, paint, ink, etc.

What is the biological activity of cis-9-octadecenoic acid?

cis-9-Octadecenoic acid has the function of regulating blood lipid and cholesterol levels and reducing the risk of atherosclerosis and cardiovascular diseases.

What is the safety and toxicity information of cis-9-octadecenoic acid?

cis-9-Octadecenoic acid is irritating to eyes, skin and respiratory tract. Wear protective glasses, gloves and masks to avoid contact.

What is the boiling point of cis-9-octadecenoic acid?

The boiling point of cis-9-octadecenoic acid is 360 ℃.

What is the pH of cis-9-octadecenoic acid?

The pH of cis-9-octadecenoic acid is pKa=4.8 (25°C).

Synthetic Use

Downstream Synthesis Route 1

• 1008-88-4
• 112-80-1

• 33421-40-8
• 87109-10-2

Reference: [1] Patent: US4386209, 1983, A,

Downstream Synthesis Route 2

• 112-80-1
• 504-40-5

• 555-43-1
• 2846-04-0

Reference: [1] Chemische Berichte, 1903, vol. 36, p. 2767[2] Chem. Zentralbl., 1904, vol. 75, # II, p. 413

* For details of the synthesis route, please refer to the original source to ensure accuracy.