Cetyl myristoleate

Cetyl myristoleate
IUPAC name Hexadecyl (Z)-tetradec-9-enoate
Identifiers
CAS number	64660-84-0
PubChem	6443825
Jmol-3D images	Image 1
SMILES CCCCCCCCCCCCCCCCOC(=O)CCCCCCC/C=C\CCCC
Properties
Molecular formula	C30H58O2
Molar mass	450.78 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cetyl myristoleate is the cetyl ester of myristoleic acid. It has multiple biological properties, including as an anti-inflammatory and a pain reliever, as well as being an immune system modulator. As supplied, it is a naturally derived, highly purified, and refined waxy ester prepared for oral administration. Because it is an ester form, highly resistant to oxidation, it has a relatively long life in the body. No harmful short or long term effects have been observed in laboratory animals at high doses or in limited human experiments. Similar substances have been used in common foods, including cheese and chocolate and even in medicines and cosmetics. It has not been found to be habit-forming and no side effects have been reported to date. It is not as well known as glucosamine and/or chondroitin although there is a growing use of cetyl myristoleate in the treatment of the body pains brought on by various maladies such as bursitis, gout, osteoarthritis, rheumatoid arthritis, fibromyalgia, and sports related injuries.

History

Cetyl Myristoleate studies began at the U.S. National Institutes of Health 25 years ago. It was discovered in the early 1960s by Harry W. Diehl [1]. Diehl was a research chemist working in sugar metabolism at the NIH in the Laboratory of Chemistry of the National Institute of Arthritis, Metabolic, and Digestive Diseases in Bethesda, Maryland. Diehl studied the seeming immunity of mice to arthritis, and discovered cetyl myristoleate through his research, investigations, testing and analysis. Diehl’s research on cetyl myristoleate was published in the March 1994 issue of the American Journal of Pharmaceutical Sciences, the journal of the American Pharmaceutical Association and the American Chemical Society. Diehl received three U.S. Patents for “use” on cetyl myristoleate, the first in 1977 on cetyl myristoleate [2], the second in 1978 for the treatment of rheumatoid arthritis [3], and then in 1996 for the treatment on osteo-arthritis [4]. After receiving his first “use” patent, Mr. Diehl immediately approached the pharmaceutical industry stalwarts, including Pfizer and Merck, with his discovery, but they declined. This was mainly due to rules concerning patents on natural products and because cetyl myristoleate could not be granted a “product” patent. Diehl knew of no other way to bring Cetyl Myristoleate to the public, and consequently his discovery sat on the shelf collecting dust until 1991 when he, himself, developed arthritis.

As Diehl got older, he began to experience some osteoarthritis in his hands, knees, and the heels of his feet. His family physician tried the usual regimen of cortisone and non-steroidal anti-inflammatory drugs without much effect on the course of the disease. Finally his physician told Harry he could not have any more cortisone. "So," Diehl said, "I thought about my discovery, and I decided to make a batch and use it on myself. " He did, and the symptoms of osteo-arthritis disappeared. Cetyl myristoleate appeared on the market as a supplement in 1991.

In May, 2000, the Federal Trade Commission, or FTC, filed separate complaints alleging "deceptive acts or practices, and the making of false advertisements" against two U.S. distributors of Cetyl myristoleate - EHP Products Inc. and CMO Distribution Centers of America, Inc. In each complaint, the FTC asserted that the distributors made claims that Cetyl myristoleate was a cure for numerous diseases.

In the case of EHP Products, the FTC charged that:

"For example, studies have not examined the efficacy of the ingredients in respondents' CMO products in the prevention or cure of arthritis, hepatitis C, emphysema, obstructive lung disease, spinal stenosis, eczema, psoriasis, fibromyalgia, tendonitis, systemic lupus erythematosus, scleroderma, temperomandibular joint disease, arthropathy, rheumatism, osteitis, osteochondritis, osteomalacia, or osteomyelitis; or in the prevention of fever blisters, colds, flu, or allergy symptoms; or in lowering cholesterol, blood pressure, or blood sugar levels. In addition, there is insufficient information available to determine the reliability of other purported studies or the applicability of such studies to the respondents' products."

A similar claim against CMO additionally took issue with the implication that a patent implied that the product was proven to be effective:

"The issuance of U.S. patents does not prove that respondents' CMO products are effective in treating or alleviating the symptoms of rheumatoid arthritis and osteoarthritis."

References

Murray, M. T. Encyclopedia of Nutritional Supplements, Prima Publishing, Rocklin, CA 1996 ISBN 0-7615-0410-9, p. 237

Sobel, D. and Klein, A. C..Arthritis: What Works.St. Martins Press, New York, NY. ISBN 0-312-92719-3 pp.221-225

Lightfoot, R.W., Jr.: "Intermittent and periodic arthritic syndromes". Arthritic and Allied Conditions. 12Th edition. Edited by D.J. McCarty, W.J. Koopman Phdadelphia, Lea & Febiger, 1993.

Fan, P.T., Yu, D Y,: "Spondyloarthropathies". Textbook of Rheuth-matology., Vol. 1, 4th edition. Edited by, Kelley, W.N., Harris, E.D., Ruddy, S., Jr., Sledge, C.B., Philadelphia W.B. Saunders. 1993.

Smiley, J.D., "Psoriatic arthritis.", Bulletin of Rheumatic Disease, 44:, 1995.

Rothman. D., et al. "Botanical Lipids. Effects in Inflammation." Immune Response, and Rheumatoid Arthritis. Seminars in Arthritis and Rheumatism, October 1995.

Bucci, L., PhD., "Glycosaminoglycan Supplements as Therapeutic Agents." Nutritional Report, January 1996.

Kremer, j., Md, "Effects of Modulation of Inflammatory and Immune Parameters in Patients with Rheumatic and Inflammatory Disease Receiving Dietary Supplementation of N-3 and N-6 Fatty Acids." Lipids, 1996.

Diehl, H., and May, E.L. "Cetyl Myristoleate Isolated from Swiss Albino Mice: An Apparent Protective Agent against Adjuvant Arthritis in Rats." Journal of Pharmaceutical Science, Vol. 83 March 1994.

External links

• FTC Complaint against EHP Products, Inc.
• FTP Complaint against CMO Distribution Centers of America, Inc.