| Identification | Back Directory | [Name]
CHOLESTA-3,5-DIENE | [CAS]
747-90-0 | [Synonyms]
Cholestadiene
CHOLESTERILENE
CHOLESTERYLENE
3,5-CHOLESTADIEN
3,5-CHOLESTADIENE
CHOLEST-3,5-DIENE
CHOLESTA-3,5-DIENE
Cholestane-3,5-diene
delta-3,5-Cholestadiene
delta-(sup3,5)-cholestadien
delta(Sup3,5)-Cholestadiene
CHOLESTA-3-5-DIENE CRYSTALLINE
CHOLESTA-3,5-DIENE, >=93% (HPLC)
delta-3,5-Cholestadien
(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene | [EINECS(EC#)]
212-021-4 | [Molecular Formula]
C27H44 | [MDL Number]
MFCD00009939 | [MOL File]
747-90-0.mol | [Molecular Weight]
368.64 |
| Chemical Properties | Back Directory | [Melting point ]
78-80 °C (lit.) | [Boiling point ]
433.93°C (rough estimate) | [density ]
0.9250 | [refractive index ]
1.4922 (estimate) | [storage temp. ]
-20°C | [form ]
Solid | [color ]
White to off-white | [biological source]
natural (organic) | [InChIKey]
RLHIRZFWJBOHHD-HKQCOZBKSA-N | [SMILES]
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C=CCC[C@]4(C)[C@H]3CC[C@]12C |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [Safety Statements ]
36 | [WGK Germany ]
3 | [RTECS ]
FZ5600000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Uses]
Cholesta-3,5-diene was used as standard in HPLC in quality analysis of different types of olive oils and edible fats. | [Definition]
ChEBI: Cholesta-3,5-diene is a cholestanoid. | [Biochem/physiol Actions]
Cholesta-3,5-diene is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis. The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation. Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells. | [in vivo]
Neutrophil Recruitment: Cholesta-3,5-diene (30 μg/ml; topical application; single dose) promotes neutrophil recruitment to tailfin wounds in transgenic zebrafish larvae (Tg(mpx:GFP)) by 6 h post-treatment1.
Tissue Regeneration: Cholesta-3,5-diene (30 μg/ml; topical application; single dose) does not enhance tissue regeneration in zebrafish tailfin wounds, unlike the lipid fraction Ft containing Cholesta-3,5-diene1.
| Animal Model: | Transgenic zebrafish larvae (Tg(mpx:GFP), 4 days post-fertilization, male/female mixed, 200-300 mg)[1] | | Dosage: | 30 μg/mL Cholesta-3,5-diene (dissolved in ethanol, diluted in E2 medium) | | Administration: | Topical application to transected tailfin immediately after wounding, single dose | | Result: | Significantly increased neutrophil accumulation at the wound site by 6 h post-treatment (2-fold vs. vehicle control.
No effect was observed in uninjured tailfins[1]. |
| Animal Model: | Transgenic zebrafish larvae (Tg(mpx:GFP), 4 days post-fertilization, male/female mixed, 200-300 mg)1 | | Dosage: | 30 μg/mL Cholesta-3,5-diene (dissolved in ethanol, diluted in E2 medium) | | Administration: | Topical application to transected tailfin immediately after wounding, single dose | | Result: | Did not promote significant tissue regeneration at 2 or 6 days post-treatment, unlike the lipid fraction Ft (which showed dose-dependent regeneration).
Resulted maximum regeneration with Ft of 50 μg/mL.
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