7,8-Didehydrocholesterol

Bezeichnung:7,8-Didehydrocholesterol

CAS-Nr434-16-2

Englisch Name:7-Dehydrocholesterol

CBNumberCB5165113

SummenformelC27H44O

Molgewicht384.64

MOL-Datei434-16-2.mol

Synonyma

7,8-Didehydrocholesterol

7,8-Didehydrocholesterol physikalisch-chemischer Eigenschaften

Schmelzpunkt	148-152 °C(lit.)
alpha	-116 º (C=1, CHCL3)
Siedepunkt	451.27°C (rough estimate)
Dichte	0.9717 (rough estimate)
Brechungsindex	1.5100 (estimate)
storage temp.	-20°C
Löslichkeit	Chloroform (Sparingly), DMSO (Slightly, Heated, Sonicated), Ethyl Acetate (Slightly)
Aggregatzustand	Solid
pka	14.91±0.70(Predicted)
Farbe	White to Yellow
Optische Aktivität	[α]20/D -115±8°, c = 1% in chloroform
Wasserlöslichkeit	Insoluble
Merck	13,2887
BRN	2224615
Stabilität	Light Sensitive
InChIKey	UCTLRSWJYQTBFZ-DDPQNLDTSA-N
LogP	9.460 (est)
CAS Datenbank	434-16-2(CAS DataBase Reference)
NIST chemische Informationen	Cholesta-5,7-dien-3-ol, (3«beta»)-(434-16-2)
EPA chemische Informationen	Cholesta-5,7-dien-3-ol, (3.beta.)- (434-16-2)

Sicherheit

S-Sätze:	24/25
WGK Germany	3
RTECS-Nr.	FZ5650000
F	8-10-23
HS Code	29061990

Gefahreninformationscode (GHS)

7-Dehydrocholesterol Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
white to off-white fine crystalline powder. It is easy to oxidize when exposed to air.
Verwenden
7-Dehydrocholesterol is a vitamin D3 precursor, which is a sterol found in animals. Vitamin D3 is produced by the action of sunlight or ultraviolet irradiation from the precursor, 7-dehydrocholesterol (7-DC), that is synthesized in the skin of animals and humans.
In most tissues of the body, 7-dehydrocholesterol is the immediate precursor of cholesterol. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. 7-DHC accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS. 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944. 7-DHC is a provitamin that is converted to vitamin D3 by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.
Definition
ChEBI: 7-Dehydrocholesterol is a 3β-sterol, a cholestanoid, a Delta(5),Delta(7)-sterol and a 3beta-hydroxy-Delta(5)-steroid. It has a role as a human metabolite and a mouse metabolite.
Allgemeine Beschreibung
7-Dehydrocholesterol, a 5,7-conjugated diene sterol is a biosynthetic precursor of cholesterol. It helps in the production of vitamin D3 when exposed to ultraviolet B (UVB) radiation. It has been used as an internal standard to determine sterols. 7-dehydrocholesterol is also used in the diagnosis of Smith-Lemli-Opitz syndrome. Blood and tissue of infants with Smith- Lemli-Opitz (SLO) syndrome contain reduced amounts of cholesterol and greatly increased concentrations of 7-dehydrocholesterol and of its isomer 8-dehydrocholesterol.
Biochem/physiol Actions
Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.

7-Dehydrocholesterol Upstream-Materialien And Downstream Produkte

7,8-Didehydrocholesterol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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