1alpha,25-Dihydroxyvitamin D2

HCID 9547243

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Basic information

CAS: 60133-18-8
Standard SMILES: C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)/C=C/[C@H](C)C(C)(C)O)CC[C@@H]23)C[C@@H](O)C[C@@H]1O
InChIKey: ZGLHBRQAEXKACO-XJRQOBMKSA-N
Molecular formula: C28H44O3
Average molar mass: 428.6 g/mol
Monoisotopic mass: 428.32904527

Overview

1alpha,25-dihydroxyvitamin D2 is a hydroxycalciol that is vitamin D2 bearing additional hydroxy substituents at positions 1alpha and 25. It has a role as a bone density conservation agent, a nutraceutical and a human xenobiotic metabolite. It is a vitamin D, a seco-ergostane and a hydroxycalciol. It is functionally related to a vitamin D2.

Names & identifiers

Preferred name: 1alpha,25-Dihydroxyvitamin D2
IUPAC: trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
English name: 1(alpha) 25-Dihydroxyvitamin D2*
Molecular formula: C28H44O3
Molecular weight: 428.65

Names & synonyms

Ercalcitriol60133-18-81,25-Dihydroxycalciferol1alpha,25-Dihydroxyvitamin D21,25-Dihydroxyvitamin D21alpha,25-dihydroxyergocalciferolRO-17-62185RWP08OQ36CHEBI:86320DTXSID904295091,3-Cyclohexanediol, 4-methylene-5-((2E)-2-((1R,3aS,7aR)-octahydro-1-((1R,2E)-5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl)-7a-methyl-4H-inden-4-ylidene)ethylidene)-, (1R,3S,5Z)-9,10-Secoergosta-5,7,10(19),22-tetraene-1,3,25-triol, (1alpha,3beta,5Z,7E,22E)-

Show more names

1-alphaH,5αRo 17-6218-Hydroxy Vitamin D2-MethylandrosteroneH-guaia-6-ene-4β-Methyl Dapagliflozin-Hydroxy Vitamin D2-d31Α,25-Dihydroxyvitamin

RefChem:1057675DTXCID3038034225-Hydroxy Doxercalciferol1alpha,25-Dihydroxycalciferol(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol1.alpha.,25-dihydroxyvitamin d2(1R,3S,Z)-5-(2-((1R,3aS,7aR,E)-1-((2R,5S,E)-6-Hydroxy-5,6-dimethylhept-3-en-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol1,25-dihydroxy Vitamin D2

Database identifiers

CAS: 60133-18-8
PubChem CID: 9547243
DTXSID: DTXSID90429509
ChEMBL: CHEMBL4303615
ChEBI: CHEBI:86320
UNII: 5RWP08OQ36
EC Number: 634-659-6
Nikkaji: J482.252H

Properties

Computed structural properties

XLogP: 4.9
Topological polar surface area: 60.7 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 5
Heavy atoms: 31
Formal charge: 0
Complexity: 758

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D2 and derivatives [ST0301]

Physical DescriptionSolid

Physicochemical properties

Boiling point: 577.7 · 577.7±50.0 °C(Predicted)
Density: 1.06 · 1.06±0.1 g/cm3(Predicted)
Flash point: 14 ℃ · 14℃
storage temp.: -20 °C · -20°C
solubility: 1 mg/ml · Ethanol: 1 mg/ml
pka: 14.43 · 14.43±0.40(Predicted)
form: Powder
color: White to off-white
biological source: synthetic
BRN: 5635017 · 5635017
Stability: Light sensitive, Temperature sensitive
InChIKey: ZGLHBRQAEXKACO-KYHOFSCESA-N
SMILES: [C@@H]1(O)C/C(=C/C=C2\CCC[C@@]3(C)[C@@]\2([H])CC[C@@H]3[C@H](C)/C=C/C(C)C(O)(C)C)/C(=C)[C@@H](O)C1
FDA UNII: 5 RWP08OQ36 · 5RWP08OQ36
UNSPSC Code: 41116107 · 41116107
NACRES: 79 · NA.79
Symbol(GHS): 6 · GHS06,GHS08
Signal word: Danger
Hazard statements: 301 · H301+H311-H330-H372
Precautionary statements: 280 · P280-P301+P310+P330-P302+P352+P312-P304+P340+P310-P314
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: T,T+,F
Risk Statements: 23 · 23/24/25-63-48/25-26-24/25-11
Safety Statements: 36 · 36/37-45-28-16-7
RIDADR: 2811 · UN 2811 6.1/PG 2
WGK Germany: 3 · 3
F: 8 · 8-10-19
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 2 InhalationAcute · Acute Tox. 2 InhalationAcute Tox. 3 DermalAcute Tox. 3 OralSTOT RE 1 Oral

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301+H311 (97.5%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety data

F: 8-10-19
PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
ridadr: UN 2811 6.1/PG 2
risk_code: 23/24/25-63-48/25-26-24/25-11
Signal word: Danger
Symbol(GHS): GHS06,GHS08
hazard_code: T,T+,F
safety_code: 36/37-45-28-16-7
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard statements: H301+H311-H330-H372
Hazard Classifications: Acute Tox. 2 InhalationAcute Tox. 3 DermalAcute Tox. 3 OralSTOT RE 1 Oral
Precautionary statements: P280-P301+P310+P330-P302+P352+P312-P304+P340+P310-P314

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Applications · 3 items

UsesThe active metabolite of Vitamin D2 (V676040).

UsesThis product may be used as an analytical standard.

General Description1α,25-Dihydroxyvitamin D2is an active form of vitamin D2. It is also known as ercalcitriol or 1α,25-dihydroxyergocalciferol. It was first isolated from mitochondria of chick kidney.