(3β)-7-Dehydro Cholesterol

Names

[ CAS No. ]:
434-16-2

[ Name ]:
(3β)-7-Dehydro Cholesterol

[Synonym ]:
delta7-Cholesterol
(3b)-7-Dehydrocholesterol
Cholesta-5,7-dien-3-ol, (3β)-
Cholesta-5,7-dien-3β-ol (8CI)
Cholesta-5,7-dien-3-β-ol
Provitamin D3
EINECS 207-100-5
Dehydrocholesterol
(3Beta)-7-Dehydro Cholesterol
(3b)-Cholesta-5,7-dien-3-ol
3β-Hydroxy-5,7-cholestadiene
Provitamine
cholesta-5,7-dien-3beta-ol
(-)-7-dehydrocholesterol
Dehydrocholesterin
(3β)-Cholesta-5,7-dien-3-ol
5,7-Cholestadien-3β-ol
7-DHC
7-Dehydrocholesterol
Provitamin D(sub 3)
MFCD00003624
Cholesta-5,7-dien-3β-ol
cholesta-5,7-dien-3b-ol
(3β)-7-Dehydrocholesterol

Biological Activity

[Description]:

7-Dehydrocholesterol is biosynthetic precursor of cholesterol and vitamin D3.

[Related Catalog]:

Natural Products >> Steroids

Research Areas >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

7-Dehydrocholesterol is a biosynthetic precursor of cholesterol and vitamin D3. 7-Dehydrocholesterol is present in relatively high concentration in skin where it is converted to pre-vitamin D3 upon UV irradiation and where it is also exposed to exogenous radical sources and oxygen[1].

[References]

[1]. Xu L, et al. Oxysterols from free radical chain oxidation of 7-dehydrocholesterol: product and mechanistic studies. J Am Chem Soc. 2010 Feb 24;132(7):2222-32.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
493.7±34.0 °C at 760 mmHg

[ Melting Point ]:
148-152 °C(lit.)

[ Molecular Formula ]:
C₂₇H₄₄O

[ Molecular Weight ]:
384.638

[ Flash Point ]:
212.3±17.9 °C

[ Exact Mass ]:
384.339203

[ PSA ]:
20.23000

[ LogP ]:
9.46

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ5650000

CHEMICAL NAME :: Cholesta-5,7-dien-3-beta-ol

CAS REGISTRY NUMBER :: 434-16-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C27-H44-O

MOLECULAR WEIGHT :: 384.71

WISWESSER LINE NOTATION :: L E5 B666 JU LUTJ A1 E1 FY1&3Y1&1 OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 60 gm/kg/2W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Tumorigenic - tumors at site of application

REFERENCE :: NATWAY Naturwissenschaften. (Springer-Verlag, Heidelberger Platz 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.1- 1913- Volume(issue)/page/year: 60,525,1973

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
FZ5650000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Smoothened adopts multiple active and inactive conformations capable of trafficking to the primary cilium.

PLoS ONE 4(4) , e5182, (2009)

Activation of Hedgehog (Hh) signaling requires the transmembrane protein Smoothened (Smo), a member of the G-protein coupled receptor superfamily. In mammals, Smo translocates to the primary cilium up...

Analysis of oxysterols and vitamin D metabolites in mouse brain and cell line samples by ultra-high-performance liquid chromatography-atmospheric pressure photoionization-mass spectrometry.

J. Chromatogr. A. 1364 , 214-22, (2014)

We have developed an ultra-high-performance liquid chromatography-atmospheric pressure photoionization-tandem mass spectrometric (UHPLC-APPI-MS/MS) method for the simultaneous quantitative analyses of...

The Essential Role of Cholesterol Metabolism in the Intracellular Survival of Mycobacterium leprae Is Not Coupled to Central Carbon Metabolism and Energy Production.

J. Bacteriol. 197 , 3698-707, (2015)

Mycobacterium leprae induces the formation of lipid droplets, which are recruited to pathogen-containing phagosomes in infected macrophages and Schwann cells. Cholesterol is among the lipids with incr...