Articles:
cholesterol 1-(9Z,12Z,15Z-octadeatrienoate)
Notes:
CE(18:3(9Z,12Z,15Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. [HMDB]
| CAS Number: | 2545-22-4 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 219-824-9 | |
| Nikkaji Web: | J192.036G | |
| Beilstein Number: | 2230688 | |
| MDL: | MFCD00041821 | |
| XlogP3-AA: | 15.20 (est) | |
| Molecular Weight: | 647.08318000 | |
| Formula: | C45 H74 O2 | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
Category: information only not used for fragrances or flavors
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
Physical Properties:
| Assay: | 95.00 to 100.00 % |
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 678.92 °C. @ 760.00 mm Hg (est) |
| Flash Point: | 689.00 °F. TCC ( 365.00 °C. ) (est) |
| logP (o/w): | 17.490 (est) |
| Soluble in: | |
| water, 2.601e-013 mg/L @ 25 °C (est) | |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). | |
Cosmetic Information:
| None found |
Suppliers:
| Santa Cruz Biotechnology |
| For experimental / research use only. |
| Cholesteryl Linolenate ≥99% |
| Sigma-Aldrich: Sigma |
| For experimental / research use only. |
| Cholesteryl Linolenate ∼98% (HPLC; detection at 205 nm) |
Safety Information:
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in Use Information:
| Category: | information only not used for fragrances or flavors | ||
| Recommendation for cholesteryl linolenate usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for cholesteryl linolenate flavor usage levels up to: | |||
| not for flavor use. | |||
Safety References:
| EPI System: | View |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA Substance Registry Services (TSCA): | 2545-22-4 |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 6436907 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 3 |
| [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate | |
| Chemidplus: | 0002545224 |
References:
| [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 6436907 |
| Pubchem (sid): | 135058553 |
Other Information:
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| KEGG (GenomeNet): | C02530 |
| HMDB (The Human Metabolome Database): | HMDB10370 |
| FooDB: | FDB027522 |
| ChemSpider: | View |
Potential Blenders and core components note
| None Found | ||
Potential Uses:
| None Found |
Occurrence (nature, food, other): note
| not found in nature |
Synonyms:
| cholest-5-en-3-ol (3b)-, (9Z,12Z,15Z)-9,12,15-octadecatrienoate | |
| (3b)- | cholest-5-en-3-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate |
| cholest-5-en-3beta-yl (Z,Z,Z)-octadeca-9,12,15-trien-1-oate | |
| cholesterol 1-(9Z,12Z,15Z-octadeatrienoate) | |
| cholesterol 1-a-linolenoate | |
| cholesterol linolenate | |
| cholesterol octadecatrienoate | |
| cholesteryl 1-(9Z,12Z,15Z-octadeatrienoate) | |
| cholesteryl 1-a-linolenoate | |
| cholesteryl octadecatrienoate | |
| [(3S,8S,9S,10R,13R,14S,17R)-10,13- | dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate |
| linolenic acid cholesteryl ester | |
| 1-a- | linolenoyl-cholesterol |
| 9,12,15- | octadecatrienoic acid, (3b)-cholest-5-en-3-yl ester, (9Z,12Z,15Z)- |