Cholesta-3,5-diene

Product NameCholesta-3,5-diene
CAS747-90-0
MFC27H44
MW368.64
EINECS212-021-4
MOL File747-90-0.mol

Chemical Properties

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 Information

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

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

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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