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Sigma-Aldrich

7-Dehydrocholesterin

≥95.0% (HPLC)

Synonym(e):

(−)-7-Dehydrocholesterin, 3β-Hydroxy-5,7-cholestadien, 5,7-Cholestadien-3β-ol, Provitamin D3

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About This Item

Empirische Formel (Hill-System):
C27H44O
CAS-Nummer:
434-16-2
Molekulargewicht:
384.64
Beilstein:
2224615
EG-Nummer:
207-100-5
MDL-Nummer:
MFCD00003624
UNSPSC-Code:
12352211
eCl@ss:
39023139
PubChem Substanz-ID:
57648485
NACRES:
NA.79

Biologische Quelle

synthetic

Assay

≥95.0% (HPLC)

Form

powder or crystals

Optische Aktivität

[α]20/D -115±8°, c = 1% in chloroform

Farbe

white to faint yellow

mp (Schmelzpunkt)

148-152 °C (lit.)

Lagertemp.

−20°C

SMILES String

[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI

1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

InChIKey

UCTLRSWJYQTBFZ-DDPQNLDTSA-N

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Allgemeine Beschreibung

7-Dehydrocholesterol (7-DHC), 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.

Anwendung

7-Dehydrocholesterol has been used as an internal standard to determine sterols.

Biochem./physiol. Wirkung

Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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7-Dehydrocholesterol (7-DHC), But Not Cholesterol, Causes Suppression of Canonical TGF-beta Signaling and Is Likely Involved in the Development of Atherosclerotic Cardiovascular Disease (ASCVD)
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Alle zugehörigen Dokumente anzeigen

Artikel

Vitamin D and Prevention of Human Disease

Vitamin D2 (ergocalciferol) is naturally synthesized from ergosterol by invertebrates, fungi, and plants in response to ultraviolet B irradiation, while vitamin D3 synthesis (cholecalciferol) is uniquely initiated in the skin of vertebrates. During sun exposure, ultraviolet B photons are absorbed by 7-dehydrocholesterol, which is found within the plasma membranes of epidermal and dermal skin layers. This reaction yields an unstable derivative of 7-dehydrocholesterol, named precholecalcitrol, which rapidly rearranges to vitamin D3. Vitamin D binding protein (DBP) is a carrier protein responsible for drawing vitamin D3 from the plasma membrane into the dermal capillaries within the extracellular space.

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