| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:30:26 UTC |
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| Update date | 2017-01-19 02:36:22 UTC |
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| FoodComEx ID | PC000394 |
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| FoodDB Record | FDB022167 |
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| Chemical Information |
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| Name | CE(16:1(9Z)) |
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| Description | CE(16:1(9Z)) is an important plasma cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Cholesteryl palmitoleate is one of the two more prevalent esters that are a component of Dehydroepiandrosterone fatty acid esters (DHEA-FA). DHEA-FA is formed from DHEA by lecithin-cholesterol acyltransferase, localized on high density lipoprotein (HDL). Once DHEA-FA is formed, it is subsequently transferred to very low density lipoprotein (VLDL) and low density lipoprotein (LDL), like cholesteryl esters. Cholesteryl palmitoleate constitutes 20% of the total lipoidal pregnenolone (an important precursor steroid) in follicular fluid. The fatty acid components of the resulting lipoidal pregnenolone derivatives resemble those of cholesteryl esters formed in plasma by the enzymatic activity of lecithin: cholesterol acyltransferase. (PMID 2770299, 8943795) [HMDB] |
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| CAS Number | 16711-66-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (Z)-Cholesterol 9-hexadecenoate | hmdb | | (Z)-Cholesterol 9-hexadecenoic acid | hmdb | | 1-palmitoleoyl-cholesterol | hmdb | | 16:1(9Z) cholesterol ester | hmdb | | CE(16:1) | hmdb | | CE(16:1/0:0) | hmdb | | CE(16:1n7/0:0) | hmdb | | CE(16:1w7/0:0) | hmdb | | cholest-5-en-3beta-yl (9Z hexadecenoate | hmdb | | cholest-5-en-3beta-yl (9Z hexadecenoate) | hmdb | | cholest-5-en-3beta-yl (9Z hexadecenoic acid | hmdb | | cholesterol 1-(9Z-hexadecenoate | hmdb | | cholesterol 1-(9Z-hexadecenoate) | hmdb | | cholesterol 1-(9Z-hexadecenoic acid | hmdb | | cholesterol 1-(9Z-hexadecenoic acid) | hmdb | | cholesterol 1-palmitoleoate | hmdb | | cholesterol 1-palmitoleoic acid | hmdb | | Cholesterol Ester(16:1) | hmdb | | Cholesterol Ester(16:1/0:0) | hmdb | | Cholesterol Ester(16:1n7/0:0) | hmdb | | Cholesterol Ester(16:1w7/0:0) | hmdb | | Cholesterol palmitoleate | hmdb | | cholesteryl 1-(9Z-hexadecenoate | hmdb | | cholesteryl 1-(9Z-hexadecenoate) | hmdb | | cholesteryl 1-(9Z-hexadecenoic acid | hmdb | | cholesteryl 1-(9Z-hexadecenoic acid) | hmdb | | cholesteryl 1-palmitoleoate | hmdb | | cholesteryl 1-palmitoleoic acid | hmdb | | Cholesteryl cis-hexadecenoate | hmdb | | Cholesteryl cis-hexadecenoic acid | hmdb | | Cholesteryl palmitoleat | hmdb | | Cholesteryl palmitoleate | hmdb | | Cholesteryl palmitoleic acid | hmdb |
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| Chemical Formula | C43H74O2 |
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| IUPAC name | (2R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl hexadec-9-enoate |
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| InChI Identifier | InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/t34-,36?,37?,38-,39?,40?,42+,43-/m1/s1 |
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| InChI Key | HODJWNWCVNUPAQ-DVQNJVTISA-N |
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| Isomeric SMILES | [H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3CC=C4CC(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCCCCCCC=CCCCCCC |
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| Average Molecular Weight | 623.0465 |
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| Monoisotopic Molecular Weight | 622.568881612 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Steroid esters |
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| Direct Parent | Cholesteryl esters |
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| Alternative Parents | |
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| Substituents | - Cholesteryl ester
- Cholesterol
- Cholestane-skeleton
- Delta-5-steroid
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 5 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Not Available |
