Palmitic acid

Chembox new
Reference= ["Merck Index", 12th Edition, 7128.]
ImageFile=Palmitic acid structure.pngImageSize=350px
IUPACName=hexadecanoic acid
Section1= Chembox Identifiers
CASNo=57-10-3
PubChem=985
SMILES=CCCCCCCCCCCCCCCC(=O)O
Section2= Chembox Properties
Formula=C₁₆H₃₂O₂
MolarMass=256.42 g/mol
Appearance=White crystals
Density=0.853 g/cm³ at 62 °C
MeltingPt=63-64 °C
BoilingPt=351-352 °C [ [http://www.inchem.org/documents/icsc/icsc/eics0530.htm Palmitic acid] at Inchem.org]
215 °C at 15 mmHg
Solubility=Insoluble
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

Palmitic acid,CH₃(CH₂)₁₄COOH or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. As its name indicates, it is a major component of the oil from palm trees (palm oil and palm kernel oil). The word palmitic is from the French "palmitique", the pith of the palm tree. Palmitic acid was discovered by Edmond Frémy in 1840, in saponified palm oil. [E. Frémy, Memoire sur les produits de la saponification de l’huile de palme, Journal de Pharmacie et de Chimie XII (1842), p. 757.] Butter, cheese, milk and meat also contain this fatty acid. [ [http://www.westonaprice.org/knowyourfats/import_sat_fat.html The Importance of Saturated Fats for Biological Functions] by Mary Enig, PhD. Wise Traditions in Food, Farming and the Healing Arts (the quarterly magazine of the Weston A. Price Foundation). Spring 2004.]

Palmitate is a term for the salts or esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiological pH. Fact|date=July 2007

Biochemistry

Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation. [ [http://www.genome.jp/kegg/pathway/map/map00061.html Fatty acid biosynthesis - Reference pathway] ]

Reduction of palmitic acid yields cetyl alcohol.

Uses

Retinyl palmitate is an antioxidant and a vitamin A compound added to low-fat milk to replace the vitamin content lost through the removal of milk fat. Palmitate is attached to the alcohol form of vitamin A, retinol, in order to make vitamin A stable in milk. Fact|date=July 2007

Derivatives of palmitic acid were used in combination with naphtha during World War II to produce napalm ("na"phthenic and "palm"itic acids). [http://www.globalsecurity.org/military/systems/munitions/napalm.htm Napalm ] ]

The WHO claims there is convincing evidence that dietary intake of palmitic acid increases risk of developing cardiovascular diseases. [ [http://www.who.int/hpr/NPH/docs/who_fao_expert_report.pdf DIET, NUTRITION AND THE PREVENTION OF CHRONIC DISEASES] , WHO Technical Report Series 916, Report of a Joint WHO/FAO Expert Consultation, World Health Organization, Geneva, 2003, p. 88 (Table)] However, possibly less-disinterested studies have shown no ill effect, or even a favorable effect, of dietary consumption of palmitic acid on blood lipids and cardiovascular disease, so that the WHO finding may be deemed controversial. [Palm oil and blood cholesterol controversy, Wikipedia] However, another study showed that palmitic acid has no hypercholesterolaemic effect if intake of linoleic acid is greater than 4.5% of energy. On the other hand, it was shown that, if the diet contains trans fatty acids, the health effects are negative, causing an LDL cholesterol increase and HDL cholesterol decrease. [cite journal |author=French MA, Sundram K, Clandinin MT |title=Cholesterolaemic effect of palmitic acid in relation to other dietary fatty acids |journal=Asia Pacific journal of clinical nutrition |volume=11 Suppl 7 |issue= |pages=S401–7 |year=2002 |pmid=12492626 |doi=]

References