64660-84-0

Usage

Uses

Used in Dietary Supplements:
Cetyl Myristoleate is used as a dietary supplement ingredient for its potential health benefits. Some research suggests that it may help in relieving pain and inflammation associated with conditions like arthritis and may support immune function. However, conclusive scientific evidence supporting these health benefits is lacking.
Used in Health and Wellness Industry:
In the health and wellness industry, cetyl myristoleate is used as a supplement ingredient for its purported benefits in managing joint pain and supporting the immune system. It is believed to have anti-inflammatory properties, which could potentially alleviate symptoms of arthritis and other inflammatory conditions. However, more research is needed to confirm these effects and establish the safety and efficacy of cetyl myristoleate supplementation.

InChI:InChI=1/C30H58O2/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-32-30(31)28-26-24-22-20-18-14-12-10-8-6-4-2/h10,12H,3-9,11,13-29H2,1-2H3/b12-10+

Synthetic route

myristoleic acid (544-64-9) + 1-Hexadecanol (36653-82-4) → cis-9-cetyl myristoleate (64660-84-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 4h; Heating;	300 mg

Methyl oleate (112-62-9) → cis-9-cetyl myristoleate (64660-84-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ozone / dichloromethane / 1 h / -78 °C 1.2: 6 h / 25 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C 2.2: 4 h / 0 - 25 °C / Reflux 3.1: Lipozyme TL 1M / 8 h / 68 °C / Enzymatic reaction View Scheme

1-Hexadecanol (36653-82-4) + myristoleic acid methyl ester (56219-06-8) → cis-9-cetyl myristoleate (64660-84-0)

Conditions	Yield
With Lipozyme TL 1M at 68℃; for 8h; Product distribution / selectivity; Enzymatic reaction;

methyl ester of azelaic acid aldehyde (1931-63-1) → cis-9-cetyl myristoleate (64660-84-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C 1.2: 4 h / 0 - 25 °C / Reflux 2.1: Lipozyme TL 1M / 8 h / 68 °C / Enzymatic reaction View Scheme

cis-9-cetyl myristoleate (64660-84-0) → myristoleic acid (544-64-9) + 1-Hexadecanol (36653-82-4)

Conditions	Yield
With sodium hydroxide In water; acetone for 14h; Heating;	A 80% B 50%

cis-9-cetyl myristoleate (64660-84-0) → cetyl myristelaidate

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / 10percent NaOH / acetone; H2O / 14 h / Heating View Scheme

Upstream product

• 112-62-9 Methyl oleate 
• 36653-82-4 1-Hexadecanol 
• 56219-06-8 myristoleic acid methyl ester 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 544-64-9 myristoleic acid 

Downstream Products

• 544-64-9 myristoleic acid 
• 36653-82-4 1-Hexadecanol 

Relevant academic research and scientific papers

Process for Preparation of Hexadecyl Cis-9-Tetradecenoate and Hexadecyl Cis-10-Tetradecenoate

Hexadecyl cis-9-tetradecenoate commonly known as Cetyl myristoleate (CMO) is being used for the treatment of osteoarthritis and other joint inflammatory diseases, cis-9-Tetradecenoic acid (cis-9-myristoleic acid) is the main precursor for the preparation of CMO. As there are limited natural plant sources for cis-9-tetradecenoic acid, the present invention aimed at the synthesis of cis-9-tetradecenoic acid methyl ester from oleic acid methyl ester. As oleic acid is not available in pure form, this has to be isolated from oleic acid-rich oils like olive oil. cis-10-Tetradecenoic acid methyl ester, an isomer of cis-9-tetradecenoic acid was also prepared from undecenoic acid methyl ester, a derivative of castor oil. Undecenoic acid is easily available commercially in pure form. Hexadecyl cis-9-tetradecenoate and hexadecyl c/s-10-tetradecenoate were prepared by enzymatic transesterification of cis-9-tetradecenoic acid methyl ester and cis-10-tetradecenoic acid methyl ester with 1-hexadecanol (cetyl alcohol) respectively. Both the isomers of cetyl myristoleate were evaluated for anti arthritis, blocking inflammation and reduction of adjuvant-induced arthritis in rats.

Cetyl myristoleate isolated from Swiss albino mice: An apparent protective agent against adjuvant arthritis in rats

Cetyl myristoleate was isolated from National Institutes of Health, general purpose, Swiss albino mice that were immune to the polyarthritis induced in rats with Freund's adjuvant. This substance, or material synthesized from cetyl alcohol and myristoleic acid, afforded good protection against adjuvant-induced arthritic states in rats. In limited comparisons, cetyl oleate, also found in Swiss albino mice, gave lesser protection, whereas cetyl myristate and cetyl elaidate, the trans-isomer of cetyl oleate, appeared to be virtually ineffective. Dosage of the protective compound as well as the site of injection of Freund's adjuvant was important.