Basic information
- CAS
434-16-2- Standard SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
UCTLRSWJYQTBFZ-DDPQNLDTSA-N- Molecular formula
- C27H44O
- Average molar mass
- 384.6 g/mol
- Monoisotopic mass
- 384.33921602
Names & identifiers
- Preferred name
- 7-Dehydrocholesterol
- IUPAC
- (3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-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
7-Dehydrocholesterol434-16-2Provitamin D3Cholesta-5,7-dien-3beta-ol7,8-Didehydrocholesterol(3beta)-Cholesta-5,7-dien-3-ol7-DHC5,7-Cholestadien-3-beta-olBK1IU07GKF(3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-olcholesta-5,7-dien-3 beta-olDTXSID20861933
Show more names
Dehydrocholesterolcholesta-5,7-dien-3β-olProvitamineCholesta-5,7-dien-3-olcholesta-5,7-dien-3-beta-ol7-DEHYDROCHOLESTEROL (7-DHC)Cholecalciferol EP Impurity B
NSC-18159CHEBI:17759Cholesta-5,7-dien-3-ol, (3beta)-provitamin D(3)(3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-3-ol10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-3-ol10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-olRefChem:105986
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
Experimental & physicochemical properties
Solubility1 mg/mL
Melting Point150.5 °C
Physical DescriptionSolid
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
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.9% (2 of 108) of reports.
H413 (98.1%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 108 reports by companies from 3 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 2 of 108 reports by companies.；There are 2 notifications provided by 106 of 108 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Status: Active Update: 18-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11283
Cholesta-5,7-dien-3-ol, (3.beta.)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAquatic Chronic 3 (98.1%)
Regulatory information
Regulatory Information
Status: Active Update: 18-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11283
Cholesta-5,7-dien-3-ol, (3.beta.)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Safety data
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationPrecursor forms of vitamins.
Tissue LocationsAdrenal Gland；Brain；Epidermis；Fibroblasts；Liver；Testis
Cellular LocationsCytoplasm；Endoplasmic reticulum；Extracellular；Membrane
Metabolite Pathways
Alendronate Action Pathway；Atorvastatin Action Pathway；Cerivastatin Action Pathway；CHILD Syndrome；Cholesteryl ester storage disease；Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)；Desmosterolosis；Fluvastatin Action Pathway；Hyper-IgD syndrome；Hypercholesterolemia；Total 23 pathways, visit the HMDB page for details
Uses & manufacturing
Use ClassificationCosmetics -> Viscosity controlling; Emulsion stabilizing
General Manufacturing InformationCholesta-5,7-dien-3-ol, (3.beta.)-: ACTIVE
Applications
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.
Related reactions
7 records
Compound notes
Loading…