“2,3-Oxidosqualene”的意思、由来-开放百科全书

词条

2,3-Oxidosqualene

释义

References
External links

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477210642
| ImageFile=2,3-oxidosqualene.svg
| ImageSize=300px
| IUPACName=2,2-Dimethyl-3-[(3E,7E,11E,15E)- 3,7,12,16,20-pentamethylhenicosa- 3,7,11,15,19-pentaenyl]oxirane
| OtherNames=Squalene oxide
2,3-Squalene oxide
Squalene epoxide
|Section1={{Chembox Identifiers
| InChI = 1/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+
| InChIKey = QYIMSPSDBYKPPY-BANQPHDMBU
| SMILES1 = CC(=CCC/C(=C/CC/C(=C/CC/C=C(\\C)/CC/C=C(\\C)/CCC1C(O1)(C)C)/C)/C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QYIMSPSDBYKPPY-BANQPHDMSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo=7200-26-2
| PubChem=5366020
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 78662
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4517951
| SMILES = O1C(C)(C)C1CC/C(=C/CC/C(=C/CC\\C=C(/C)CC\\C=C(/C)CC\\C=C(/C)C)C)C
| MeSHName=2,3-oxidosqualene
|Section2={{Chembox Properties
| Formula=C₃₀H₅₀O
| MolarMass=426.717 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}(S)-2,3-Oxidosqualene ((S)-2,3-epoxysqualene) is an intermediate in the synthesis of the cell membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed when squalene is oxidized by the enzyme squalene monooxygenase. 2,3-Oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.^[1]

The stereoisomer 2,3-(R)-oxidosqualene is an inhibitor of lanosterol synthase.

References

1. ^{{cite journal|author=Abe I.|year= 2007|title=Enzymatic synthesis of cyclic triterpenes|journal=Natural Product Reports|volume=24|pages=1311–31|pmid=18033581| doi = 10.1039/b616857b|issue=6}}

External links

[https://dx.doi.org/10.2210/rcsb_pdb/mom_2007_12 Oxidosqualene cyclase, PDB December 2007 Molecule of the Month]

2 : Epoxides|Triterpenes

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