Cetyl myristoleate

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Cetyl myristoleate
Cetyl myristoleate.svg
Identifiers
CAS number 64660-84-0 YesY
PubChem 6443825
ChemSpider 4947787 N
Jmol-3D images Image 1
Properties
Molecular formula C30H58O2
Molar mass 450.78 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

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

Animal pharmacology[edit]

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[edit]

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[edit]

  1. ^ a b c Ameye, Laurent G; Chee, Winnie SS (2006). Arthritis Research & Therapy 8 (4): R127. doi:10.1186/ar2016. 
  2. ^ a b c 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, 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.