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Merck
CN

30800

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
NACRES:
NA.79
PubChem Substance ID:
57648485
eCl@ss:
39023139
UNSPSC Code:
12352211
EC Number:
207-100-5
MDL number:
MFCD00003624
Beilstein/REAXYS Number:
2224615

Key Documents

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Product Name

7-Dehydrocholesterol, ≥95.0% (HPLC)

InChI key

UCTLRSWJYQTBFZ-DDPQNLDTSA-N

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

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

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

Quality Level

100

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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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3140
BCCK9520
BCCL8081
BCCJ4317
BCCG8559

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Vitamin D, Calcium, and the Epidermis
Vitamin D, 1, 527-544 (2018)
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)
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)
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
P E Jira et al.
Journal of lipid research, 41(8), 1339-1346 (2000-08-18)
The Smith-Lemli-Opitz syndrome (SLOS) is caused by deficient Delta(7)-dehydrocholesterol reductase, which catalyzes the final step of the cholesterol biosynthetic pathway, resulting in low cholesterol and high concentrations of its direct precursors 7-dehydrocholesterol (7DHC) and 8DHC. We hypothesized that i) 7DHC
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