Anacardic acid

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. [cite journal
journal = Nature
volume = 174
pages = 604
year = 1954
doi = 10.1038/174604a0
title = Olefinic Nature of Anacardic Acid from Indian Cashew-nut Shell Liquid
author = V. J. Paul & L. M. Yeddanapalli ] 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.

Use against tooth abcesses

Chembox new
Name=Anacardic acid (C15:3, all-"Z", major component)
ImageFile=Anacardic acid C15-3.svg
ImageSize=
IUPACName=2-hydroxy-6- [(8"Z",11"Z")-pentadeca-8,11,14-trienyl] benzoic acid
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Section1= Chembox Identifiers
CASNo=
PubChem=9875131
SMILES=C=CCC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
MeSHName=anacardic+acid
Section2= Chembox Properties
Formula=C₂₂H₃₀O₃
MolarMass=342.4718 g/mol
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
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Autoignition= 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. [ 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 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. [ 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.] Heating these anacardic acids converts them to the alcohols (cardinols) but does not destroy their activity [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.] unless high heat is used, which decarboxylates them. [ 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.] It is said that the people of the Gold Coast use cashew leaves and bark for a toothache. [http://www.hort.purdue.edu/newcrop/duke_energy/Anacardium_occidentale.html#Folk%20Medicine Cashew plants in folk medicine.]

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.cite journal|title=A Nutty Chemical |date=September 8, 2008 |volume=86 |issue=36 |pages=26-27 |author=Alexander H. Tullo |journal=Chemical and Engineering News]

History

The first chemical analysis of the oil of the cashew nut shell from the Anacardium occidentale was published in 1847. [cite journal
journal = Annalen der Chemie und Pharmacie
volume = 63
issue = 2
year = 1847
title = Ueber die eigenthümlichen Bestandtheile der Anacardiumfrüchte
author = Dr. Städeler
doi = 10.1002/jlac.18470630202
pages = 137–164] It was later found to be a mixture rather than one chemical, sometimes the plural anacardic acids is used.

ynergies

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.Fact|date=January 2008 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). [ [http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/2006/54/i20/abs/jf061481u.html Bioactivity of Anacardic Acid against Colorado Potato Beetle (Leptinotarsa decemlineata) Larvae] ]

Anacardic acid kills MRSA cells more rapidly than totarol. [ [http://cat.inist.fr/?aModele=afficheN&cpsidt=3094896 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] ]

ee also

* List of phytochemicals and foods in which they are prominent

References