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Sigma-Aldrich

7-Dehydrocholesterol

≥95.0% (HPLC)

Synonym(s):

(−)-7-Dehydrocholesterol, 3β-Hydroxy-5,7-cholestadiene, 5,7-Cholestadien-3β-ol, Provitamin D3

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
434-16-2
Molecular Weight:
384.64
Beilstein/REAXYS Number:
2224615
EC Number:
207-100-5
MDL number:
MFCD00003624
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
57648485
NACRES:
NA.79

biological source

synthetic

assay

≥95.0% (HPLC)

form

powder or crystals

optical activity

[α]20/D -115±8°, c = 1% in chloroform

color

white to faint yellow

mp

148-152 °C (lit.)

storage temp.

−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

InChI key

UCTLRSWJYQTBFZ-DDPQNLDTSA-N

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General description

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.

Application

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

Biochem/physiol Actions

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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)
Huang SS, et al.
Journal of Cellular Biochemistry, 118(6), 1387-1387 (2017)
Nicholas A Robinson et al.
BMC genomics, 18(1), 971-971 (2017-12-17)
Farmed and wild Atlantic salmon are exposed to many infectious and non-infectious challenges that can cause mortality when they enter the sea. Exercise before transfer promotes growth, health and survival in the sea. Swimming performance in juveniles at the freshwater
Wendy A Gold et al.
American journal of medical genetics. Part A, 173(8), 2246-2250 (2017-06-03)
GMPPA encodes the GDP-mannose pyrophosphorylase A protein (GMPPA). The function of GMPPA is not well defined, however it is a homolog of GMPPB which catalyzes the reaction that converts mannose-1-phosphate and guanosine-5'-triphosphate to GDP-mannose. Previously, biallelic mutations in GMPPA were
Amaranth oil increased fecal excretion of bile acid but had no effect in reducing plasma cholesterol in hamsters
de Castro lIA, et al.
Lipids, 48, 609-618 (2013)
Vitamin D, Calcium, and the Epidermis
Vitamin D, 1, 527-544 (2018)
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Articles

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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