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Anacardic acids are chemical compounds found in the shell of the cashew nut (Anacardium occidentale). As they are closely related to urushiol
Urushiol

Urushiol is an organic oil toxin found in plants of the Linnaean taxonomy 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

The skin is the outer covering of the body, also known as the epidermis. It is the largest organ of the integumentary system made up of multiple layers of epithelial biological tissue, and guards the underlying muscles, bones, ligaments and organ s....
 rash on contact, known as urushiol-induced contact dermatitis
Urushiol-induced contact dermatitis

Urushiol-induced contact dermatitis is the medical name given to allergy rashes produced by the oil urushiol, which is contained in various plants, including the plants of the genus Toxicodendron , as well as other plants in the family Anacardiaceae , and also unrelated plants such as Ginkgo biloba....
. 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 chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s. Each consists of a salicylic acid
Salicylic acid

Salicylic acid is a beta hydroxy acid with the chemical formula C6H4COOH, where the OH group is adjacent to the carboxylic acid....
 substituted with an alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 chain that has 15 or 17 carbon atoms. The alkyl group may be saturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
 or unsaturated; anacardic acid is a mixture of saturated and unsaturated molecules.






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Anacardic acids are chemical compounds found in the shell of the cashew nut (Anacardium occidentale). As they are closely related to urushiol
Urushiol

Urushiol is an organic oil toxin found in plants of the Linnaean taxonomy 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

The skin is the outer covering of the body, also known as the epidermis. It is the largest organ of the integumentary system made up of multiple layers of epithelial biological tissue, and guards the underlying muscles, bones, ligaments and organ s....
 rash on contact, known as urushiol-induced contact dermatitis
Urushiol-induced contact dermatitis

Urushiol-induced contact dermatitis is the medical name given to allergy rashes produced by the oil urushiol, which is contained in various plants, including the plants of the genus Toxicodendron , as well as other plants in the family Anacardiaceae , and also unrelated plants such as Ginkgo biloba....
. 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 chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s. Each consists of a salicylic acid
Salicylic acid

Salicylic acid is a beta hydroxy acid with the chemical formula C6H4COOH, where the OH group is adjacent to the carboxylic acid....
 substituted with an alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 chain that has 15 or 17 carbon atoms. The alkyl group may be saturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
 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 abcesses, it is also active against acne
Acne

Acne is a group of skin rashes that have different causes.* Acne vulgaris - most commonly experienced around puberty, typically of the face and shoulders/chest...
, some insects, tuberculosis
Tuberculosis

Tuberculosis is a common and often deadly infectious disease caused by mycobacterium, mainly Mycobacterium tuberculosis . Tuberculosis usually attacks the lungs but can also affect the central nervous system, the lymphatic system, the circulatory system, the genitourinary system, the gastrointestinal system, bones, joints, and even the...
, and MRSA. It is primarily found in foods such as cashew
Cashew

The cashew is a tree in the flowering plant family Anacardiaceae. The plant is native to northeastern Brazil. Its English language name derives from the Portuguese language name for the fruit of the cashew tree, caju, which in turn derives from the indigenous Tupi language name, acaj?....
 nuts, cashew apples, and cashew shell oil, but also in mango
Mango

Mangoes belong to the genus Mangifera, consisting of numerous species of tropical fruiting trees in the flowering plant family Anacardiaceae....
, Pelargonium
Pelargonium

Pelargonium is a genus of flowering plants which includes about 200 species of perennial plants, succulent plants, and shrubs, commonly known as geraniums or storksbills....
 geraniums.

Use against tooth abcesses


The side chain with three unsaturated bonds was the most active against Streptococcus mutans
Streptococcus mutans

Streptococcus mutans is a Gram-positive, Facultative anaerobic organism bacteria commonly found in the human oral cavity and is a significant contributor to dental caries....
, the tooth decay bacterium, in test tube experiments. The number of unsaturated bonds were 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 vulgaris; 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 is a common and often deadly infectious disease caused by mycobacterium, mainly Mycobacterium tuberculosis . Tuberculosis usually attacks the lungs but can also affect the central nervous system, the lymphatic system, the circulatory system, the genitourinary system, the gastrointestinal system, bones, joints, and even the...
 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....
 use cashew leaves and bark for a toothache.

Industrial uses


Anacardic acid is the main component of cashew nutshell liquid
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....
 (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 , with a good workable pot life....
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 anethole
Anethole

Anethole is an aromatic compound that occurs widely in nature, in essential oils. It contributes a large component of the distinctive flavors of anise and fennel , Syzygium anisatum , licorice , and star anise ....
 from the seed of anise
Anise

is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and southwest Asia known for its flavor that resembles licorice, fennel, and tarragon....
 (Umbelliferae) and linalool
Linalool

Linalool is a naturally-occurring terpene alcohol chemical found in many flowers and spice plants with many commercial applications, the majority of which are based on its pleasant scent ....
 from green tea in vitro (in the test tube) [Muroi & Kubo, p1782]. The totarol 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 also. 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
Breast cancer

Breast cancer is a cancer that starts in the Cell of the breast in women and men. Worldwide, breast cancer is the second most common type of cancer after lung cancer and the fifth most common cause of cancer death....
. [Kubo et al, 1993]

Anacardic acid (2-hydroxy-6-alkylbenzoic acid) provides resistance to small pest insects (aphids and spider mites).

Anacardic acid kills MRSA cells more rapidly than totarol.

See also

  • List of phytochemicals and foods in which they are prominent
    List of phytochemicals and foods in which they are prominent

    While there is ample evidence to support the health benefits of diets rich in fruits, vegetables, legumes, whole grains and nuts, evidence that these effects are due to specific nutrients or phytochemicals is limited....