7-Dehydrocholesterol

Available from stock

7-Dehydrocholesterol

SKU
D0331

Category:

Synonyms
7-DHC , NSC 18159 , Provitamin D3 , 7-Cholesterol , (-)-7-Dehydrocholesterol , 3-β-Hydroxy-5,7-cholestadiene , 5,7-Cholestadien-3-bet-ol
434-16-2
CAS-Number
C27H44O
Molecular Formula
384.64
Molecular Weight

Specifications

Purity
≥95% (HPLC)
Appearance
White to off-white powder
Identity
1H-NMR

Properties

Solvents
ethanol, chloroform, ethyl acetate, DMSO (slightly), water
Melting Point
150-151 °C (anhydr)
Boiling Point
493.74 °C at 760 mmHg (Predicted)
Optical Activity
[α]20/D -116º, c = 1 in CHCl3
Refractive Index
n20D 1.54 (Predicted)
Density
1.00 g/cm3 (Predicted)

Documentation

Safety Data Sheet (SDS)
CDX D0331 MSDS.pdf
Shipping
AMBIENT
Short Term Storage
+4°C
Long Term Storage
-20°C
Handling Advice
Protect from light and moisture.
Use / Stability
Stable for at least 2 years after receipt when stored at -20°C.
Transportation
Not dangerous goods
Description
Precursor of cholesterol and vitamin D3. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. Mutations in the gene encoding DHCR7 lead to increased levels of 7-DHC and the neurodevelopmental syndrome Smith-Lemli-Opitz syndrome (SLOS). 7-DHC is used as a biomarker for SLOS screenings. Inhibits human fibroblast sphingomyelinase. Shown to have cytotoxic effects on melanoma cells. In skin, photolysis of 7-DHC by ultraviolet light produces vitamin D3. UV/Vis: λmax 271, 282, 293nm.
Smiles
O[C@H](C1)CC[C@@]2(C)C1=CC=C3[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C)C)C
InChi Key
UCTLRSWJYQTBFZ-DDPQNLDTSA-N
References
(1) T. Okano, et al.: J. Nutr. Sci. Vitaminol. 24, 47 (1978) , (2) J.c. Maziere, et al.: BBRC 100, 1299 (1981) , (3) Q. Xiong, et al.: Chem. Phys. Lipids 115, 1 (2002) , (4) A. Valencia, et al.: Free. Radic. Biol. Med. 41, 1704 (2006) , (5) M. Gelzo, et al.: Free. Radic. Biol. Med. 70, 129 (2014) , (6) W. Liu, et al.: J. Lipid. Res. 55, 329 (2014)
InChi
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

Precursor of cholesterol and vitamin D3. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. Mutations in the gene encoding DHCR7 lead to increased levels of 7-DHC and the neurodevelopmental syndrome Smith-Lemli-Opitz syndrome (SLOS). 7-DHC is used as a biomarker for SLOS screenings. Inhibits human fibroblast sphingomyelinase. Shown to have cytotoxic effects on melanoma cells. In skin, photolysis of 7-DHC by ultraviolet light produces vitamin D3. UV/Vis: λmax 271, 282, 293nm.

SKU: D0331 Category:

Additional information

Synonyms

7-DHC, NSC 18159, Provitamin D3, 7-Cholesterol, (-)-7-Dehydrocholesterol, 3-β-Hydroxy-5,7-cholestadiene, 5,7-Cholestadien-3-bet-ol
Purity

≥95% (HPLC)
Appearance

White to off-white powder
CAS-Number

434-16-2
Molecular Formula

C27H44O
Molecular Weight

384.64
Identity

1H-NMR
Solvents

ethanol, chloroform, ethyl acetate, DMSO (slightly), water
Melting Point

150-151 °C (anhydr)
Boiling Point

493.74 °C at 760 mmHg (Predicted)
Optical Activity

[α]20/D -116º, c = 1 in CHCl3
Refractive Index

n20D 1.54 (Predicted)
Density

1.00 g/cm3 (Predicted)
Smiles

O[C@H](C1)CC[C@@]2(C)C1=CC=C3[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C)C)C
InChi Key

UCTLRSWJYQTBFZ-DDPQNLDTSA-N
Shipping

AMBIENT
Short Term Storage

+4°C
Long Term Storage

-20°C
Handling Advice

Protect from light and moisture.
Use / Stability

Stable for at least 2 years after receipt when stored at -20°C.
Transportation

Not dangerous goods
References

(1) T. Okano, et al.: J. Nutr. Sci. Vitaminol. 24, 47 (1978), (2) J.c. Maziere, et al.: BBRC 100, 1299 (1981), (3) Q. Xiong, et al.: Chem. Phys. Lipids 115, 1 (2002), (4) A. Valencia, et al.: Free. Radic. Biol. Med. 41, 1704 (2006), (5) M. Gelzo, et al.: Free. Radic. Biol. Med. 70, 129 (2014), (6) W. Liu, et al.: J. Lipid. Res. 55, 329 (2014)
InChi

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
Quantity

10 g, 25 g, Bulk

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