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14-September-2008 18:38:38 - Anacardic acid General structure of anacardic acids. R is an alkyl chain of variable length, which may be saturated or unsaturated. General structure of anacardic acids. R is an alkyl chain of variable length, which may be saturated or unsaturated. Anacardic acids are chemical compounds found in the shell of the cashew nut Anacardium occidentale. As they are closely related to urushiol, they also cause an allergic skin rash on contact, known as urushiol-induced contact dermatitis. Anacardic acid is a yellow liquid. It is miscible partially in alcohol and ether, but nearly immiscible in water. Chemically, anacardic acid is a mixture of several closely related organic compounds. Each consists of a salicylic acid substituted with an alkyl chain that has 15 or 17 carbon atoms. The alkyl group may be saturated or unsaturated; anacardic acid is a mixture of saturated and unsaturated molecules. The exact mixture depends on the species of the plant. 1 of which the 15 carbon unsaturated side chain found in the cashew plant is very lethal to gram positive bacteria. Primarily used for tooth abcesses, it is also active against acne, some insects, tuberculosis, and MRSA. It is primarily found in foods such as cashew nuts, cashew apples, and cashew shell oil, but also in mango, garden geranium. Contents 1 Use against tooth abcesses 2 Industrial uses 3 History 4 Synergies 5 Other and potential uses 6 See also 7 References Use against tooth abcesses Anacardic acid C15:3, all-Z, major component IUPAC name 2-hydroxy-6-8Z,11Z-pentadeca-8,11,14-trienylbenzoic acid Identifiers CAS number PubChem 9875131 MeSH anacardic+acid SMILES C=CCC=CCC=CCCCCCCCC1=CC=CC=C1OC=OO Properties Molecular formula C22H30O3 Molar mass 342.4718 g/mol Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references The side chain with three unsaturated bonds was the most active against Streptococcus mutans, the tooth decay bacterium, in test tube experiments. The number of unsaturated bonds were not material against Propionibacterium acnes, the acne bacterium.2 Eichbaum claims that one part to 200,000 to as high as 2,000,000 parts of solution of anacardic acid is lethal to gram positive bacteria in 15 minutes in vitro. Somewhat higher ratios killed tubercle bacteria of tuberculosis in 30 minutes.3 Heating these anacardic acids converts them to the alcohols cardinols but does not destroy their activity4 unless high heat is used, which decarboxylates them.5 It is said that the people of the Gold Coast use cashew leaves and bark for a toothache.6 Industrial uses Anacardic acid is the main component of cashew nutshell liquid CNSL, and finds use in the chemical industry for the production of cardanol, which is used for resins, coatings, and frictional materials. Cardanol is used to make phenalkamines, which are used as curing agents for the durable epoxy coatings used on concrete floors.7 History The first chemical analysis of the oil of the cashew nut shell from the Anacardium occidentale was published in 1847.8 It was later found to be a mixture rather than one chemical, sometimes the plural anacardic acids is used. Synergies Anacardic acid is synergistic with anethole from the seed of anise Umbelliferae and linalool from green tea in vitro in the test tube Muroi Kubo, p1782. The totarol in the bark of Podocarpus trees is synergistic with anacardic acid also.citation needed It is especially potent against acne. Other and potential uses There is also a suspicion that anacardic acids inhibit the growth of cancer tumors such as breast cancer. Kubo et al, 1993 Anacardic acid 2-hydroxy-6-alkylbenzoic acid provides resistance to small pest insects aphids and spider mites.9 Anacardic acid kills MRSA cells more rapidly than totarol.10 See also List of phytochemicals and foods in which they are prominent References ^ V. J. Paul L. M. Yeddanapalli 1954. Olefinic Nature of Anacardic Acid from Indian Cashew-nut Shell Liquid. Nature 174: 604. doi:10.1038/174604a0. ^ Kubo I, Muroi H, Himejima M. 1993 Structure - Antibacterial activity relationships of anacardic acids. Journal of Agricultural food Chemicals 41; 1016-1019, on p1018. ^ Eichbaum FW 1946 Biological properties of anacardic acid O- pentadeca dienylsalicylic acid and related compounds. General discussion-bactericidal action. Memorias do Instituto Butanen 19 71-86. ^ Himejima M Kubo I. 1991 Antibacterial agents from the cashew Anacardium occidentale Anacardiaceae nutshell oil. Journal of Agricultural Food Chemicals 39; 418-421, on p419. ^ Patel NM Patel MS 1936 Cashew-nut shell oil and a study of the changes produced in the oil by the action of heat. Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences, Medicine 5 pt2 114-131. ^ http://www.hort.purdue.edu/newcrop/duke_energy/Anacardium_occidentale.html#Folk%20Medicine Cashew plants in folk medicine. ^ Alexander H. Tullo September 8, 2008. A Nutty Chemical. Chemical and Engineering News 86 36: 26-27. ^ Dr. Städeler 1847. Ueber die eigenthümlichen Bestandtheile der Anacardiumfrüchte. Annalen der Chemie und Pharmacie 63 2: 137-164. doi:10.1002/jlac.18470630202. ^ Bioactivity of Anacardic Acid against Colorado Potato Beetle Leptinotarsa decemlineata Larvae ^ Journal of applied bacteriology J. appl. bacteriol. ISSN 0021-8847 CODEN JABAA4, 1996, vol. 80, no4, pp. 387-394 29 ref., Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus Retrieved from http://en..org/wiki/Anacardic_acid Categories: Antiseptics | Benzoic acids | Hydroxy acids | PhenolsHidden categories: All articles with statements | Articles with statements since January 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page This page was last modified on 9 September 2008, at 12:19
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