Cetyl myristoleate

Cetyl myristoleate

Names
IUPAC name Hexadecyl (Z)-tetradec-9-enoate
Other names cis-9-Cetyl myristoleate
Identifiers
CAS Number	64660-84-0
3D model (Jmol)	Interactive image
ChemSpider	4947787
PubChem	6443825
UNII	87P8K33Q5X
InChI InChI=1S/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- Key: DYIOQMKBBPSAFY-BENRWUELSA-N 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- Key: DYIOQMKBBPSAFY-BENRWUELBX
SMILES CCCCCCCCCCCCCCCCOC(=O)CCCCCCC/C=C\CCCC
Properties
Chemical formula	C30H58O2
Molar mass	450.79 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cetyl myristoleate is a chemical compound which is a type of fatty acid ester or, more specifically, a cetylated fatty acid (CFA). It is the cetyl ester of myristoleic acid. Although it is used as a dietary supplement, there is little clinical evidence to support a benefit for any medical condition.^[1]

Synthesis

Cetyl myristoleate has been prepared by an esterification reaction between myristoleic acid and cetyl alcohol, catalyzed by p-toluenesulfonic acid monohydrate.^[2]

Animal pharmacology

In animal studies, cetyl myristoleate was first reported to block inflammation and prevent adjuvant-induced arthritis at very high doses in rats.^[2][3] Other studies using identical and similar methods have failed to replicate this effect.^[4] In follow-up studies in mice, a modest anti-inflammatory effect was observed.^[2]

Study in humans

Although cetyl myristoleate is sold as a dietary supplement, its possible benefits in the treatment of any medical condition are largely unknown^[1] and the Federal Trade Commission has taken legal action against supplement manufacturers for exaggerated claims.^[5]

There is some clinical evidence for the benefits of CFAs, which may contain cetyl myristoleate, in arthritic patients.^[6] One pilot study found that cetyl myristoleate may be beneficial against fibromyalgia.^[7] However, these low-quality clinical trials provide only limited scientific evidence of efficacy.^[1]

References

1. Ameye, Laurent G; Chee, Winnie SS (2006). "From nutraceuticals to functional foods". Arthritis Research & Therapy. 8 (4): R127. doi:10.1186/ar2016.
2. Hunter, Kenneth W; Gault, Ruth A; Stehouwer, Jeffrey S; Tam-Chang, Suk-Wah (2003). "Synthesis of cetyl myristoleate and evaluation of its therapeutic efficacy in a murine model of collagen-induced arthritis". Pharmacological Research. 47 (1): 43–7. doi:10.1016/S1043-6618(02)00239-6. PMID 12526860.
3. H.W Diehl, E.L May (1994). "Cetyl myristoleate isolated from Swiss albino mice: an apparent protective agent against adjuvant arthritis in rats". J Pharm Sci. 83 (3): 296–9. doi:10.1002/jps.2600830307. PMID 8207671.
4. Whitehouse, MW; McGeary, RP (1999). "Concerning the anti-arthritic action of cetyl myristoleate in rats: An interim report". Inflammopharmacology. 7 (3): 303–10. doi:10.1007/s10787-999-0014-z. PMID 17638102.
5. See for example:
   • DOCKET NO. C-3896 Archived April 21, 2013, at the Wayback Machine., Federal Trade Commission
   • FTC Complaint against EHP Products, Inc.
   • FTP Complaint against CMO Distribution Centers of America, Inc.
6. Hesslink Jr, R; Armstrong d, 3rd; Nagendran, MV; Sreevatsan, S; Barathur, R (2002). "Cetylated fatty acids improve knee function in patients with osteoarthritis". The Journal of rheumatology. 29 (8): 1708–12. PMID 12180734.
7. A.M Edwards (2001). "CMO (cerasomol-cis-9-cetyl myristoleate) in the treatment of fibromyalgia: an open pilot study". J. Nutr. Environ. Med. 11 (2): 105–111. doi:10.1080/13590840120060849.