| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:09:59 UTC |
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| Update date | 2019-11-26 03:06:09 UTC |
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| Primary ID | FDB012091 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Anacardic acid |
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| Description | Found in cashew nut shell
Anacardic acids are chemical compounds found in the shell of the cashew nut (Anacardium occidentale). 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; anacardic acid is a mixture of saturated and unsaturated molecules. The exact mixture depends on the species of the plant and the major component is C5:3 all-Z. |
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| CAS Number | 103904-74-1 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Anacardate | Generator | | (15:2)-Anacardic acid | HMDB | | 2-Hydroxy-6-(8,11-pentadecadienyl)-(Z,Z)-benzoic acid | HMDB | | 2-Hydroxy-6-(8Z,11Z)-8,11-pentadecadien-1-yl-benzoic acid | HMDB | | Anacardic acid diene | HMDB | | 2-Hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoate | Generator | | Benzoic acid, 2-hydroxy-6-(8,11-pentadecadienyl)-, (Z,Z)- | manual | | Benzoic acid, 2-hydroxy-6-(8Z,11Z)-8,11-pentadecadien-1-yl- | manual |
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| Predicted Properties | |
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| Chemical Formula | C22H32O3 |
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| IUPAC name | 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid |
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| InChI Identifier | InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h4-5,7-8,15,17-18,23H,2-3,6,9-14,16H2,1H3,(H,24,25)/b5-4-,8-7- |
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| InChI Key | KAOMOVYHGLSFHQ-UTOQUPLUSA-N |
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| Isomeric SMILES | CCC\C=C/C\C=C/CCCCCCCC1=C(C(O)=O)C(O)=CC=C1 |
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| Average Molecular Weight | 344.4877 |
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| Monoisotopic Molecular Weight | 344.23514489 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Benzoic acids and derivatives |
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| Direct Parent | Salicylic acids |
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| Alternative Parents | |
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| Substituents | - Salicylic acid
- Benzoic acid
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Vinylogous acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Biological location: Source: |
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| Role | Biological role: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 76.70%; H 9.36%; O 13.93% | DFC |
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| Melting Point | Mp 25-26° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Anacardic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00xr-2921000000-e8cfe2a19fc08dd61fc4 | Spectrum | | Predicted GC-MS | Anacardic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-4704900000-312b95cecb769b1cc38f | Spectrum | | Predicted GC-MS | Anacardic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Anacardic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-1029000000-1c006ff8be091bc98439 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f6t-7956000000-3946fdbefd02d9f18e6b | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-3920000000-e4c2c005a187b27cba9e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0007-0069000000-8dec51893da3aa8bc11f | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0092000000-72c001bfc57b828f48f9 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-1290000000-f2c31a6187b07fac82de | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0119000000-8309caef0bfe8a677975 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052b-4595000000-398d788100a917a69a30 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0693-9500000000-37e1dd3de2033d9d0adf | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0019000000-eabf76621e8dfe5f7a8a | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0294000000-7a525af1df4de6d1df18 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-3960000000-7d0a6e1a243cf5f3d32f | 2021-09-25 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 9998782 |
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| ChEMBL ID | CHEMBL451725 |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 11824131 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB33896 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HDC45-S:HDC46-T |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | ANACARDIC-ACID |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Anacardic_acid |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| Anti-acne | 50177 | An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin. | DUKE | | Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | | Anti prostaglandin | 49020 | An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort. | DUKE | | Anti septic | 33281 | An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management. | DUKE | | Anti thrombotic | 50248 | An agent that prevents blood clot formation, reducing the risk of thrombosis. Its biological role is to inhibit platelet aggregation and blood coagulation. Therapeutically, it is used to prevent and treat conditions such as stroke, heart attack, and deep vein thrombosis, as well as to manage atrial fibrillation and peripheral artery disease. | DUKE | | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | | Aphicide | | An insecticide that targets and kills aphids, used to control infestations in crops and gardens, helping to prevent damage and reduce disease transmission. | DUKE | | Dermatitigenic | | An agent that causes inflammation of the skin (dermatitis), triggering allergic reactions and immune responses. Its biological role involves activating immune cells, leading to skin irritation. Therapeutically, it is used to test skin sensitivity and develop treatments for dermatitis. Key medical uses include diagnosing skin allergies and researching dermatitis treatments. | DUKE | | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | | Lipoxygenase inhibitor | 35856 | An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases. | DUKE | | Molluscicide | 33904 | An agent that kills mollusks, particularly snails and slugs, playing a key role in controlling vectors of parasitic diseases. Therapeutically, it is used to prevent the spread of schistosomiasis and other snail-borne diseases, with medical applications in public health and epidemiology. | DUKE | | Nematicide | 25491 | An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health. | DUKE | | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | | Prostaglandin-synthetase inhibitor | 23924 | An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, menstrual cramps, and fever, by inhibiting the enzyme responsible for prostaglandin synthesis, thereby alleviating symptoms. | DUKE | | Protisticide | | An agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections. | DUKE | | Schistosomicide | | An agent destructive to schistosomes, used to treat schistosomiasis, a disease caused by blood flukes transmitted by snails. Therapeutically, it eliminates the parasites, reducing inflammation and preventing long-term damage. Key medical uses include treating and preventing schistosomiasis in endemic regions, particularly in Africa, Brazil, and Asia. | DUKE | | Tyrosinase inhibitor | 59997 | An agent that blocks the activity of tyrosinase, an enzyme involved in melanin production, reducing skin pigmentation. Therapeutically used to treat hyperpigmentation disorders, such as melasma and vitiligo, and as a skin-lightening agent in dermatology. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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