Anacardic acid
Encyclopedia
Urushiol
Urushiol is an oily organic allergen found in plants of the family Anacardiaceae, especially Toxicodendron spp. . It causes an allergic skin rash on contact, known as urushiol-induced contact dermatitis...
, they also cause an allergic skin
Skin
-Dermis:The dermis is the layer of skin beneath the epidermis that consists of connective tissue and cushions the body from stress and strain. The dermis is tightly connected to the epidermis by a basement membrane. It also harbors many Mechanoreceptors that provide the sense of touch and heat...
rash on contact, known as urushiol-induced contact dermatitis
Urushiol-induced contact dermatitis
Urushiol-induced contact dermatitis is the medical name given to allergic rashes produced by the oil urushiol, which is contained in various plants, including the plants of the genus Toxicodendron , other plants in the family Anacardiaceae Urushiol-induced contact dermatitis (also called...
. 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 compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
s. Each consists of a salicylic acid
Salicylic acid
Salicylic acid is a monohydroxybenzoic acid, a type of phenolic acid and a beta hydroxy acid. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. It is derived from the metabolism of salicin...
substituted with an alkyl chain that has 15 or 17 carbon atoms. The alkyl group may be saturated
Saturation (chemistry)
In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...
or unsaturated; anacardic acid is a mixture of saturated and unsaturated molecules. The exact mixture depends on the species of the plant. of which the 15 carbon unsaturated side chain found in the cashew plant is very lethal to Gram positive bacteria.
Primarily used for tooth abscess
Tooth abscess
A tooth abscess or root abscess is pus enclosed in the tissues of the jaw bone at the apex of an infected tooth's root. Usually the abscess originates from a bacterial infection that has accumulated in the soft, often dead, pulp of the tooth. This can be caused by untreated tooth decay, cracked...
es, it is also active against acne
Acne
Acne is a general term used for acneiform eruptions. It is usually used as a synonym for acne vulgaris, but may also refer to:*Acne aestivalis*Acne conglobata*Acne cosmetica*Acne fulminans*Acne keloidalis nuchae*Acne mechanica...
, some insects, tuberculosis
Tuberculosis
Tuberculosis, MTB, or TB is a common, and in many cases lethal, infectious disease caused by various strains of mycobacteria, usually Mycobacterium tuberculosis. Tuberculosis usually attacks the lungs but can also affect other parts of the body...
, and MRSA. It is primarily found in foods such as cashew
Cashew
The cashew is a tree in the family Anacardiaceae. Its English name derives from the Portuguese name for the fruit of the cashew tree, caju, which in turn derives from the indigenous Tupi name, acajú. It is now widely grown in tropical climates for its cashew nuts and cashew apples.-Etymology:The...
nuts, cashew apples, and cashew nutshell oil
Cashew nutshell liquid
The cashew nutshell liquid or cashew shell oil is a natural resin found in the honeycomb structure of the cashew nutshell. It consists of about 90% anacardic acids and 10% cardol...
, but also in mango
Mango
The mango is a fleshy stone fruit belonging to the genus Mangifera, consisting of numerous tropical fruiting trees in the flowering plant family Anacardiaceae. The mango is native to India from where it spread all over the world. It is also the most cultivated fruit of the tropical world. While...
s and Pelargonium
Pelargonium
Pelargonium is a genus of flowering plants which includes about 200 species of perennials, succulents, and shrubs, commonly known as scented geraniums or storksbills. Confusingly, Geranium is the correct botanical name of a separate genus of related plants often called Cranesbills. Both Geranium...
geraniums.
Experimental antibacterial properties
The side chain with three unsaturated bonds was the most active against Streptococcus mutansStreptococcus mutans
Streptococcus mutans is a facultatively aerobic, Gram-positive coccus-shaped bacterium commonly found in the human oral cavity and is a significant contributor to tooth decay.The microbe was first described by J Kilian Clarke in 1924.-Introduction:...
, the tooth decay bacterium, in test tube experiments. The number of unsaturated bonds was not material against Propionibacterium acnes
Propionibacterium acnes
Propionibacterium acnes is a relatively slow growing, typically aerotolerant anaerobic gram positive bacterium that is linked to the skin condition acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery...
, the acne bacterium. 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
Tuberculosis
Tuberculosis, MTB, or TB is a common, and in many cases lethal, infectious disease caused by various strains of mycobacteria, usually Mycobacterium tuberculosis. Tuberculosis usually attacks the lungs but can also affect other parts of the body...
in 30 minutes. Heating these anacardic acids converts them to the alcohols (cardanol
Cardanol
Cardanol is a phenol obtained from anacardic acid, the main component of cashew nutshell liquid , a byproduct of cashew nut processing. Cardanol finds use in the chemical industry in resins, coatings, frictional materials, and surfactants used as pigment dispersants for water-based inks...
s), but does not destroy their activity unless high heat is used, which decarboxylates them. It is said that the people of the Gold Coast
Gold Coast (region)
The Gold Coast was the region of West Africa which is now the nation of Ghana. Early uses of the term refer literally to the coast and not the interior. It was not until the 19th century that the term came to refer to areas that are far from the coast...
use cashew leaves and bark for a toothache.
Industrial uses
Anacardic acid is the main component of cashew nutshell liquidCashew nutshell liquid
The cashew nutshell liquid or cashew shell oil is a natural resin found in the honeycomb structure of the cashew nutshell. It consists of about 90% anacardic acids and 10% cardol...
(CNSL), and finds use in the chemical industry for the production of cardanol
Cardanol
Cardanol is a phenol obtained from anacardic acid, the main component of cashew nutshell liquid , a byproduct of cashew nut processing. Cardanol finds use in the chemical industry in resins, coatings, frictional materials, and surfactants used as pigment dispersants for water-based inks...
, which is used for resins, coatings, and frictional materials. Cardanol is used to make phenalkamine
Phenalkamine
Phenalkamines are a distinct range of natural epoxy curing agents that provide very fast cure, even at low temperatures Phenalkamines are a distinct range of natural epoxy curing agents that provide very fast cure, even at low temperatures Phenalkamines are a distinct range of natural epoxy curing...
s, which are used as curing agents for the durable epoxy coatings used on concrete floors.
History
The first chemical analysis of the oil of the cashew nut shell from the Anacardium occidentale was published in 1847. 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 anetholeAnethole
Anethole is a phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils...
from the seed of anise
Anise
Anise , Pimpinella anisum, also called aniseed, is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and Southwest Asia. Its flavor resembles that of liquorice, fennel, and tarragon.- Biology :...
(Umbelliferae) and linalool from green tea in vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...
[Muroi & Kubo, p1782]. The totarol
Totarol
Totarol is a a meroterpene natural phenol. It is naturally produced phenolic diterpene that is bioactive as -totarol. It was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand. Podocarpus totara was investigated for unique molecules...
in the bark of Podocarpus
Podocarpus
Podocarpus is a genus of conifers, the most numerous and widely distributed of the podocarp family Podocarpaceae. The 105 species of Podocarpus are evergreen shrubs or trees from 1-25 m in height...
trees is synergistic with anacardic acid in its bactericidal effects.
Other and potential uses
There is also a suspicion that anacardic acids inhibit the growth of cancer tumors such as breast cancerBreast cancer
Breast cancer is cancer originating from breast tissue, most commonly from the inner lining of milk ducts or the lobules that supply the ducts with milk. Cancers originating from ducts are known as ductal carcinomas; those originating from lobules are known as lobular carcinomas...
. [Kubo et al., 1993]
Anacardic acid (2-hydroxy-6-alkylbenzoic acid) provides resistance to small pest insects (aphids and spider mites).
Anacardic acid kills methicillin-resistant Staphylococcus aureus
Methicillin-resistant Staphylococcus aureus
Methicillin-resistant Staphylococcus aureus is a bacterium responsible for several difficult-to-treat infections in humans. It is also called multidrug-resistant Staphylococcus aureus and oxacillin-resistant Staphylococcus aureus...
(MRSA) cells more rapidly than totarol
Totarol
Totarol is a a meroterpene natural phenol. It is naturally produced phenolic diterpene that is bioactive as -totarol. It was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand. Podocarpus totara was investigated for unique molecules...
.