| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-18 23:22:28 UTC |
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| Updated at | 2020-12-07 19:06:58 UTC |
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| CannabisDB ID | CDB006172 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Linoleic acid |
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| Description | Linoleic acid is a doubly unsaturated fatty acid or polyunsaturated fatty acid (PUFA). It is also known as an omega-6 fatty acid, occurring widely in plant glycosides. In linoleic acid the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Linoleic acid is a colorless or white oil with a faint, fatty odor. Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and the lipids of cell membranes. Altered levels of linoleic acid have been found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Conjugated linoleic acids have been studied for their beneficial effects in the prevention and treatment of many diseases, including obesity, cancer, diabetes, and cardiovascular diseases (PMID: 27636835 ). Linoleic acid can be found in all living organisms, ranging from bacteria to humans, although it cannot be synthesized by mammals. In rats, a diet deficient in linoleate (the salt form of the acid) has been shown to cause mild skin scaling, hair loss, (PMID: 9144095 ) and poor wound healing (PMID: 10498749 ). Linoleic acid is abundant in many nuts, fatty seeds (flax seeds, hemp seeds, poppy seeds, sesame seeds, etc.) and their derived vegetable oils; comprising over half (by weight) of poppy seed, safflower, sunflower, corn, and soybean oils. Linoleic acid is used in making quick-drying oils, which are useful in oil paints and varnishes. Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. A number of reports have identified linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the skin (PMID: 9692305 ; PMID: 9749992 ). Linoleic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C18H32O2 |
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| Average Molecular Weight | 280.45 |
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| Monoisotopic Molecular Weight | 280.2402 |
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| IUPAC Name | (2E)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-N,N'-bis[2-(4-hydroxyphenyl)ethyl]butanediimidic acid |
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| Traditional Name | (2E)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-N,N'-bis[2-(4-hydroxyphenyl)ethyl]butanediimidic acid |
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| CAS Registry Number | 2197-37-7 |
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| SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- |
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| InChI Key | OYHQOLUKZRVURQ-HZJYTTRNSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. |
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| Kingdom | Organic compounds |
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| Super Class | Lignans, neolignans and related compounds |
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| Class | Not Available |
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| Sub Class | Not Available |
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| Direct Parent | Lignans, neolignans and related compounds |
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| Alternative Parents | |
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| Substituents | - Norlignan skeleton
- Cinnamic acid amide
- Cinnamic acid or derivatives
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Fatty amide
- Fatty acyl
- Benzenoid
- N-acyl-amine
- Carboxamide group
- Secondary carboxylic acid amide
- Ether
- Carboxylic acid derivative
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic nitrogen compound
- Carbonyl group
- Organonitrogen compound
- 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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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Biological role: Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -8.5 °C | Not Available | | Boiling Point | 229 °C at 16 mmHg | Wikipedia | | Water Solubility | 0.14 mg/L | Wikipedia | | logP | 7.05 | SANGSTER (1993) |
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| Predicted Properties | [] |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Cannabisin G, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Cannabisin G, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Cannabisin G, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Cannabisin G, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| General References | - Fuke G, Nornberg JL: Systematic evaluation on the effectiveness of conjugated linoleic acid in human health. Crit Rev Food Sci Nutr. 2017 Jan 2;57(1):1-7. doi: 10.1080/10408398.2012.716800. [PubMed:27636835 ]
- Cunnane SC, Anderson MJ: Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and [1-14C]linoleate oxidation. J Lipid Res. 1997 Apr;38(4):805-12. [PubMed:9144095 ]
- Ruthig DJ, Meckling-Gill KA: Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6. J Nutr. 1999 Oct;129(10):1791-8. doi: 10.1093/jn/129.10.1791. [PubMed:10498749 ]
- Letawe C, Boone M, Pierard GE: Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones. Clin Exp Dermatol. 1998 Mar;23(2):56-8. doi: 10.1046/j.1365-2230.1998.00315.x. [PubMed:9692305 ]
- Ando H, Ryu A, Hashimoto A, Oka M, Ichihashi M: Linoleic acid and alpha-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin. Arch Dermatol Res. 1998 Jul;290(7):375-81. doi: 10.1007/s004030050320. [PubMed:9749992 ]
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