Cetyl myristoleate

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.[1] There are some clinical trials appearing to show benefit for inflammation due to arthritis which should be taken into account.[2]

Cetyl myristoleate
Names
IUPAC name
Hexadecyl (Z)-tetradec-9-enoate
Other names
cis-9-Cetyl myristoleate
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
C30H58O2
Molar mass 450.792 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis

Cetyl myristoleate has been prepared by an esterification reaction between myristoleic acid and cetyl alcohol, catalyzed by p-toluenesulfonic acid monohydrate.[3]

Animal pharmacology

In animal studies, cetyl myristoleate was first reported to block inflammation and prevent adjuvant-induced arthritis at very high doses in rats.[3][4] Other studies using identical and similar methods have failed to replicate this effect.[5] In follow-up studies in mice, a modest anti-inflammatory effect was observed.[3]

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.[6]

There is some clinical evidence for the benefits of CFAs, which may contain cetyl myristoleate, in arthritic patients.[7] One pilot study found that cetyl myristoleate may be beneficial against fibromyalgia,[8] and there have been other studies.[2] However, these low-quality clinical trials provide only limited scientific evidence of efficacy.[1]

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References
  1. Ameye, Laurent G; Chee, Winnie SS (2006). "From nutraceuticals to functional foods". Arthritis Research & Therapy. 8 (4): R127. doi:10.1186/ar2016. PMC 1779427. PMID 16859534.
  2. "Has CM8® - Cetyl Myristoleate Had Clinical Trials? - Yes It Has!". CM8. Retrieved 2020-03-31.
  3. 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. CiteSeerX 10.1.1.549.2557. doi:10.1016/S1043-6618(02)00239-6. PMID 12526860.
  4. 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.
  5. 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.
  6. 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.
  7. See cetyl-myristoleate.com/clinical-studies; and 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.
  8. 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.
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