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Cholesterol, 7-dehydro-

HCID 172
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
434-16-2
Standard SMILES
CC(C)CCCC(C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC21C
InChIKey
UCTLRSWJYQTBFZ-UHFFFAOYSA-N
Molecular formula
C27H44O
Average molar mass
384.6 g/mol
Monoisotopic mass
384.33921602

Overview

7-dehydrocholesterol has been reported in Neonectria ditissima and Lactarius with data available.

Names & identifiers

Preferred name
Cholesterol, 7-dehydro-
IUPAC
10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
English name
7-Dehydrocholesterol
Molecular formula
C27H44O
Molecular weight
384.64

Names & synonyms

.DELTA.7-CholesterolCholesterol, 7-dehydro-(-)-7-Dehydrocholesterol.DELTA.5,7-CholesterolCholesta-5,7-dien-3-beta-ol5,7-Cholestandien-3.beta.-ol(3.beta.)-Cholesta-5,7-dien-3-olCholesta-5,7-dien-3.beta.-ols5386Cholesta-5,7-dien-3-ol, (3.beta.)-SCHEMBL287700Cholesta-5,7-dien-3-.beta.-ol
Show more names
7-DHCPROVITAMIN D3Dehydrocholesterolcholesta-5,7-dien-3β-olProvitamineCholesta-5,7-dien-3-ol7,8-Didehydrocholesterol7-DEHYDROCHOLESTEROL (7-DHC)Cholecalciferol EP Impurity B
NSC181595,7-Cholestadien-3|A-ol monohydrateAKOS01591628817-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-olFL159095DB-051079NS00010100ST50409145

Database identifiers

CAS

Properties

Computed structural properties

XLogP
8
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
5
Heavy atoms
28
Formal charge
0
Complexity
643

Physicochemical properties

Melting point
148 · 148-152 °C(lit.)
Boiling point
451.27 °C · 451.27°C (rough estimate)
alpha
-116 · -116 º (C=1, CHCL3)
Density
0.9717 · 0.9717 (rough estimate)
refractive index
1.51 · 1.5100 (estimate)
storage temp.
-20 °C · -20°C
solubility
Chloroform (Sparingly), DMSO (Slightly, Heated, Sonicated), Ethyl Acetate (Slightly)
pka
14.91 · 14.91±0.70(Predicted)
form
Solid
color
White to Yellow
biological source
synthetic
optical activity
20 · [α]20/D -115±8°, c = 1% in chloroform
Water Solubility
Insoluble
Merck
13 · 13,2887
BRN
2224615 · 2224615
Stability
Light Sensitive

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
8-10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
FZ5650000
hs_code
29061990
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses7-Dehydrocholesterol is a vitamin D3 precursor, which is a sterol found in animals. Vitamin D3 is produced by the action of sunlight or ultraviolet irradiation from the precursor, 7-dehydrocholesterol (7-DC), that is synthesized in the skin of animals and humans.In most tissues of the body, 7-dehydrocholesterol is the immediate precursor of cholesterol. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. 7-DHC accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS. 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944. 7-DHC is a provitamin that is converted to vitamin D3 by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.

General Description7-Dehydrocholesterol, 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. It has been used as an internal standard to determine sterols. 7-dehydrocholesterol is also used in the diagnosis of Smith-Lemli-Opitz syndrome. Blood and tissue of infants with Smith- Lemli-Opitz (SLO) syndrome contain reduced amounts of cholesterol and greatly increased concentrations of 7-dehydrocholesterol and of its isomer 8-dehydrocholesterol.

Upstream & downstream products

Upstream raw materials

Cholesterol

Downstream products

Vitamin D3Δ8(14)-Cholestenol(3beta,6Z)-9,10-secocholesta-5(10),6,8-trien-3-ol

Related reactions

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New reaction record

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
434-16-2
PubChem CID
172
Cosmetics Ingredients Functions
VISCOSITY CONTROLLINGSKIN CONDITIONINGEMULSION STABILISING
InChIKey
UCTLRSWJYQTBFZ-DDPQNLDTSA-N
SMILES
[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
LogP
9.46 · 9.460 (est)
CAS DataBase Reference
434 · 434-16-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
1 IU07GKF · BK1IU07GKF
NIST Chemistry Reference
-5 · Cholesta-5,7-dien-3-ol, (3«beta»)-(434-16-2)
EPA Substance Registry System
-5 · Cholesta-5,7-dien-3-ol, (3.beta.)- (434-16-2)
UNSPSC Code
41116107 · 41116107
NACRES
79 · NA.79
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
24 · 24/25
WGK Germany
3 · 3
RTECS
5650000 · FZ5650000
F
8 · 8-10-23
TSCA
TSCA listed
HS Code
29061990 · 29061990
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Active
LATHOSTEROL
DELTA-4,6-CHOLESTADIENOL (30 MG)
5α-Cholesta-8,14-dien-3β-ol

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海策嵘生物科技有限公司[email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海宝博洛新材料科技有限公司15572878882; 15572878882 · [email protected]
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上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
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上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
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TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海皓之翔生物科技有限公司(原上海拓青化工有限公司)526763801 13301653310 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
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BOC Sciences16314854226 · [email protected]
南京艾比克斯生化科技有限公司025-87193546 18652950785 · [email protected]
南京熙朗化工产品有限公司18936048580 · [email protected]
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Chemaphor Chemical Services.(613) 656-7272 · [email protected]
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成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
深圳市森迪生物科技有限公司18126413629 0755-23311925 2355327053 · [email protected]
济南晟齐医药科技有限公司0531-88892685 18660160628 · [email protected]
深圳市森迪生物科技有限公司18124570582 TEL:0755-23574479 2355327139 · [email protected]

Additional notes

DefinitionChEBI: 7-Dehydrocholesterol is a 3β-sterol, a cholestanoid, a Delta(5),Delta(7)-sterol and a 3beta-hydroxy-Delta(5)-steroid. It has a role as a human metabolite and a mouse metabolite.