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7-Dehydrocholesterol
- Iupac Name：(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
- CAS No.: 434-16-2
- Molecular Weight：384.648
- Modify Date.: 2022-11-29 12:06
- Introduction: A vitamin precursor.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.
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1. Names and Identifiers
- 1.1 Name
- 7-Dehydrocholesterol
- 1.2 Synonyms
(-)-7-dehydrocholesterol (3)-7-Dehydrochlesterol (3b)-7-Dehydrocholesterol (3b)-Cholesta-5,7-dien-3-ol (3Beta)-7-Dehydro Cholesterol (3beta)-Cholesta-5,7-dien-3-ol (3-beta)-cholesta-7-dien-3-ol (3beta)-cholesta-7-dien-3-ol (3Β)-7-Dehydrocholesterol (3Β)-Cholesta-5,7-dien-3-ol 3-Hydroxycholesta-5,7-diene 3Β-Hydroxy-5,7-cholestadiene 5,7-Cholestadien-3Β-ol 7-DHC cholesta-5,7-dien-3-beta-ol cholesta-5,7-dien-3beta-ol cholesta-5,7-dien-3b-ol Cholesta-5,7-dien-3-ol Cholesta-5,7-dien-3-ol, (3beta)- Cholesta-5,7-dien-3-ol, (3Β)- Cholesta-5,7-dien-3-Β-ol Cholesta-5,7-dien-3Β-ol Cholesta-5,7-dien-3Β-ol (8CI) Dehydrocholesterin Dehydrocholesterol delta7-Cholesterol EINECS 207-100-5 MFCD00003624 Provitamin D(sub 3) Provitamin D3 Provitamine Δ5,7-cholesterol
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- 1.3 CAS No.
- 434-16-2
- 1.4 CID
- 439423
- 1.5 EINECS(EC#)
- 207-100-5
- 1.6 Molecular Formula
- C27H44O (isomer)
- 1.7 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
- 1.8 InChIkey
- UCTLRSWJYQTBFZ-DDPQNLDTSA-N
- 1.9 Canonical Smiles
- CC(C)CCCC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C
- 1.10 Isomers Smiles
- C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
2. Properties
- 2.1 Density
- 1
- 2.1 Melting point
- 147-151℃
- 2.1 Boiling point
- 493.7 °C at 760 mmHg
- 2.1 Refractive index
- 1.535
- 2.1 Flash Point
- 212.3 °C
- 2.1 Precise Quality
- 384.33900
- 2.1 PSA
- 20.23000
- 2.1 logP
- 7.30880
- 2.1 Appearance
- Solid
- 2.2 Chemical Properties
- white to off-white fine crystalline powder
- 2.3 Physical
- Solid
- 2.4 pKa
- 14.91±0.70(Predicted)
- 2.5 Water Solubility
- Insoluble
- 2.6 StorageTemp
- -20°C
3. Use and Manufacturing
- 3.1 GHS Classification
-
GHS Hazard StatementsAggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory.
Reported as not meeting GHS hazard criteria by 2 of 3 companies. For more detailed information, please visit
ECHA C&L websiteOf the 1 notification(s) provided by 1 of 3 companies with hazard statement code(s):
H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
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.
Precautionary Statement Codes
P273, and P501
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- 3.2 Usage
- A vitamin precursor.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.
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4. Safety and Handling
- 4.1 Risk Statements
- S24/25
- 4.1 Safety Statements
- S24/25
- 4.1 Hazard Declaration
- H413
- 4.1 RIDADR
- OTH
- 4.1 Caution Statement
- P273, P501
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- FZ5650000
- 4.1 Safety
- Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.
- 4.2 Specification
-
white to off-white fine crystalline powder
usageEng:A vitamin precursor.
Safety Statements:24/25
24/25:Avoid contact with skin and eyes
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | H413 May cause long lasting harmful effects to aquatic life |
| Precautionary statement(s) | |
| Prevention | P273 Avoid release to the environment. |
| Response | none |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
434-16-2Total: 42 Synthesis Route
9. Other Information
- 9.0 Mesh
- Precursor forms of vitamins. (See all compounds classified as Provitamins.)
- 9.1 Mesh Entry Terms
- 7,8-didehydrocholesterol
- 9.2 Manufacturing Info
- Cholesta-5,7-dien-3-ol, (3.beta.)-: ACTIVE
- 9.3 Use Classification
- Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]|Cosmetics -> Emulsion stabilizing; Viscosity controlling
- 9.4 Merck
- 13,2887
- 9.5 BRN
- 2224615
- 9.6 Description
- 7-dehydro Cholesterol (7-DHC) is an immediate precursor of cholesterol.1 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.1,2 It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS.1 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 (Item No. 14611).1 7-DHC is a provitamin that is converted to vitamin D3 (Item No. 11792) by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.3,4
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- 9.7 Chemical Properties
- white to off-white fine crystalline powder
- 9.8 Uses
- A vitamin precursor.
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. - View all
- 9.9 Uses
- 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. 7-Dehydrocholesterol has been used as an internal standard to determine sterols.
7-dehydrocholesterol is 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.
- 9.10 Uses
- A vitamin D3 precursor.
- 9.11 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.
10. Computational chemical data
- Molecular Weight: 384.648g/mol
- Molecular Formula: C27H44O
- Compound Is Canonicalized: True
- XLogP3-AA: 8
- Exact Mass: 384.339216023
- Monoisotopic Mass: 384.339216023
- Complexity: 643
- Rotatable Bond Count: 5
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 20.2
- Heavy Atom Count: 28
- Defined Atom Stereocenter Count: 7
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcfB4IAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGCAAAAAGgAACAAADxSggAICAAAAAgCAAiBCAAAAAAAgAAAACAAAAAgIEAIAAQAAQAAEwAAIgAOAwPAPgAAAAAAAAADAAAQAACAAAQAACAAAAA==
11. Question & Answer
-
7-Dehydrocholesterol is a chemical substance that belongs to a class of white crystalline powders with no odor and insoluble in water. However, it has a wide range of uses and plays an important role..
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