Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:35 UTC |
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Update date | 2019-11-26 02:58:12 UTC |
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Primary ID | FDB002943 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Gamolenic acid |
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Description | A minor component of many animal lipids
Although GLA is an n?6 fatty acid, a type of acid which is generally pro-inflammatory, it has anti-inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary GLA.); An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) -- Pubchem; From GLA, the body forms dihomo-?-linolenic acid (DGLA). This is one of the body's three sources of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH1, which in turn forms PGE1 and the thromboxane TXA1. PGE1 has a role in regulation of immune system function and is used as the medicine alprostadil. TXA1 modulates the pro-inflammatory properties of the thromboxane TXA2.; GLA is categorized as an n?6 (also called ??6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ?) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n?6). Chemically, GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of ?-linolenic acid, which is the n?3 fatty acid found in flax seed.; The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by ?6-desaturase (D6D), an enzyme which allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states where there is excessive consumption of GLA metabolites.; ?-Linolenic acid (gamma-linolenic acid or GLA, sometimes called gamoleic acid) is a fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases. The efficacy of such use is disputed. |
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CAS Number | 506-26-3 |
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Structure | |
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Synonyms | Synonym | Source |
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Gamolenate | Generator | (6,9,12)-linolenate | biospider | (6,9,12)-linolenic acid | biospider | (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid | biospider | (6Z,9Z,12Z)-Octadecatrienoate | biospider | (6Z,9Z,12Z)-Octadecatrienoic acid | biospider | (Z,Z,Z)-6,9,12-Octadecatrienoate | biospider | (Z,Z,Z)-6,9,12-Octadecatrienoic acid | biospider | «gamma»-linolenic acid | biospider | 18:3 (N-6) | ChEBI | 6-cis,9-cis,12-cis-Octadecatrienoate | Generator | 6-cis,9-cis,12-cis-Octadecatrienoic acid | biospider | 6,9,12-all-cis-Octadecatrienoate | biospider | 6,9,12-all-cis-Octadecatrienoic acid | biospider | 6,9,12-Octadecatrienoate | biospider | 6,9,12-Octadecatrienoic acid | biospider | 6,9,12-Octadecatrienoic acid, (6Z,9Z,12Z)- | biospider | 6,9,12-Octadecatrienoic acid, (Z,Z,Z)- | biospider | 6(Z),9(Z),12(Z)-Octadecatrienoate | biospider | 6(Z),9(Z),12(Z)-Octadecatrienoic acid | biospider | 6Z,9Z,12Z-octadecatrienoate | biospider | 6Z,9Z,12Z-octadecatrienoic acid | biospider | Acido gamolenico | biospider | Acidum gamolenicum | biospider | all-cis-6,9,12-octadecatrienoate | biospider | all-cis-6,9,12-octadecatrienoic acid | biospider | C18:3 (N-6) | ChEBI | C18:3, N-6,9,12 all-cis | ChEBI | cis-6, cis-9, cis-12-octadecatrienoic acid | biospider | cis-6,cis-9,cis-12-Octadecatrienoic acid | biospider | cis-Delta(6,9,12)-octadecatrienoate | biospider | cis-Delta(6,9,12)-octadecatrienoic acid | biospider | cis-δ(6,9,12)-octadecatrienoate | Generator | cis-δ(6,9,12)-octadecatrienoic acid | Generator | cis,cis,cis-6,9,12-Octadecatrienoic acid | biospider | Efamast | biospider | Efemast | db_source | Efomase | db_source | Epogam | db_source | g-Linolenate | Generator | g-Linolenic acid | db_source | g-Linolensaeure | Generator | Gamma-linolenate | biospider | Gamma-linolenic acid | biospider | gamma-Linolensaeure | ChEBI | Gamma-llnolenic acid | biospider | Gammalinolenic acid | db_source | Gammolin | db_source | Gamoleate | Generator | Gamoleic acid | ChEBI | Gamolenic acid | biospider | Gamolenic acid (inn) | biospider | Gamolenic acid [inn:ban] | biospider | Gamolenic acid, BAN, INN | db_source | GLA | db_source | Ligla | biospider | Octadeca-6,9,12-triensaeure | ChEBI | Unigam | db_source | Viacutan | biospider | γ-linolenate | Generator | γ-linolenic acid | Generator | γ-linolensaeure | Generator |
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Predicted Properties | |
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Chemical Formula | C18H30O2 |
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IUPAC name | (6Z,9E,12Z)-octadeca-6,9,12-trienoic acid |
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InChI Identifier | InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9+,13-12- |
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InChI Key | VZCCETWTMQHEPK-XQYVMNDBSA-N |
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Isomeric SMILES | CCCCC\C=C/C\C=C\C\C=C/CCCCC(O)=O |
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Average Molecular Weight | 278.4296 |
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Monoisotopic Molecular Weight | 278.224580204 |
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Classification |
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Description | Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Lineolic acids and derivatives |
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Direct Parent | Lineolic acids and derivatives |
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Alternative Parents | |
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Substituents | - Octadecanoid
- Long-chain fatty acid
- Fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 77.65%; H 10.86%; O 11.49% | DFC |
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Melting Point | Not Available | |
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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 | Not Available |
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External Links |
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ChemSpider ID | 4444436 |
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ChEMBL ID | CHEMBL464982 |
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KEGG Compound ID | C06426 |
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Pubchem Compound ID | 5280933 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28661 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03073 |
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CRC / DFC (Dictionary of Food Compounds) ID | CPL98-G:CPL99-H |
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EAFUS ID | Not Available |
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Dr. Duke ID | GAMMA-LINOLENIC-ACID |
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BIGG ID | 48234 |
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KNApSAcK ID | C00001226 |
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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 | gamma-Linolenic 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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Alpha-reductase inhibitor | 23924 | An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats conditions like benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing sebum production and slowing hair loss. | DUKE | 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-aggregant | | An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots. | DUKE | Anti-alcoholic | 52217 | An agent that reduces alcohol cravings and withdrawal symptoms, commonly used in managing alcohol dependence and addiction, aiding in the treatment of alcohol use disorder by blocking the rewarding aspects of alcohol consumption. | DUKE | Anti-arthritic | 52217 | An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life. | DUKE | Anti asphyctic | | An agent that enhances the blood's ability to carry oxygen, playing a crucial role in preventing hypoxia. Therapeutically, it is used to treat conditions where oxygen delivery is compromised, such as high-altitude sickness, anemia, and respiratory disorders, improving oxygenation and reducing symptoms of asphyxiation. | DUKE | Anti-atherosclerotic | 38070 | An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes. | DUKE | Anti eczemic | 52217 | An agent that reduces inflammation and itching, commonly used to manage eczema symptoms, atopic dermatitis, and other skin allergies, providing relief and preventing flare-ups. | DUKE | Anti hypercholesterolemic | | An agent that prevents or controls an increase of cholesterol in the blood, playing a crucial role in reducing cardiovascular risk. Therapeutically, it helps manage hypercholesterolemia, preventing plaque buildup and lowering the risk of heart disease, making it a key treatment for conditions like atherosclerosis and coronary artery disease. | DUKE | Anti-menorrhagic | 52217 | An agent that reduces heavy menstrual bleeding, playing a biological role in regulating menstrual flow. Therapeutically, it is used to treat menorrhagia, with key medical applications including managing excessive uterine bleeding, dysmenorrhea, and menstrual disorders. | DUKE | Anti monosodium-glutamate | | An antidote for MSG poisoning, neutralizing excessive glutamate effects. Biologically, it regulates glutamate levels, mitigating neurotoxicity. Therapeutically, it's used to treat MSG-induced adverse reactions, such as headaches and nausea, and may have applications in managing conditions like migraines and neuropathic pain. | DUKE | Anti-obesity | 52217 | An agent that reduces body weight, commonly used in managing obesity and related disorders, by regulating appetite, metabolism, and fat storage, with therapeutic applications in preventing chronic diseases such as diabetes and cardiovascular disease. | DUKE | Anti premenstrual syndrome | 52217 | An agent that alleviates symptoms of premenstrual syndrome (PMS), reducing physical and emotional discomfort. Its biological role involves regulating hormonal fluctuations, and its therapeutic applications include managing mood swings, bloating, and breast tenderness. Key medical uses include treating PMS, premenstrual dysphoric disorder (PMDD), and other menstrual-related disorders. | DUKE | Anti-prostatitic | | An agent that relieves prostatitis, reducing inflammation of the prostate gland, and is used to treat benign prostatic hyperplasia (BPH) and chronic pelvic pain syndrome. | DUKE | Anti Raynaud's | 52217 | An agent that improves blood flow to extremities, reducing vasospasm and relieving symptoms of Raynaud's disease, commonly used to manage cold-induced digital ulcers, pain, and discoloration in fingers and toes. | 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 | Hypocholesterolemic | | An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease. | DUKE | Hypotensive | | An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications. | DUKE | Immunomodulator | 50846 | An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis. | DUKE | Vasodilator | 35620 | An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Bile acid-CoA:amino acid N-acyltransferase | BAAT | Q14032 | Cytosolic acyl coenzyme A thioester hydrolase | ACOT7 | O00154 | Acyl-coenzyme A thioesterase 2, mitochondrial | ACOT2 | P49753 | Acyl-coenzyme A thioesterase 4 | ACOT4 | Q8N9L9 | Acyl-coenzyme A thioesterase 8 | ACOT8 | O14734 | Acyl-coenzyme A thioesterase 1 | ACOT1 | Q86TX2 |
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Pathways | Name | SMPDB Link | KEGG Link |
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Alpha Linolenic Acid and Linoleic Acid Metabolism | SMP00018 | map00592 |
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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 | show |
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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 | — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — 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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