(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadeca-7,9-dien-5-ol

• ChemBase ID: 107836
• Molecular Formular: C27H44O
• Molecular Mass: 384.63766
• Monoisotopic Mass: 384.33921603
• 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
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=CC=C2[C@]1(C)CC[C@@H](C2)O)C)C
• 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
• InChIKey: UCTLRSWJYQTBFZ-DDPQNLDTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-5-ol; (1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
• IUPAC Traditional name: dehydrocholesterol
• Synonyms: 7-DEHYDROCHOLESTEROL; (-)-7-Dehydrocholesterol; 3β-Hydroxy-5,7-cholestadiene; 5,7-Cholestadien-3β-ol; Provitamin D3; 7-Dehydrocholesterol; Cholesta-5,7-dien-3β-ol; 7,8-Didehydrocholesterol; 7-Dehydrocholesterin; Provitamin D3.; (3β)-7-Dehydro Cholesterol

Database IDs

• CAS Number: 434-16-2
• EC Number: 207-100-5
• MDL Number: MFCD00003624
• Beilstein Number: 2224615
• PubChem SID: 162093552; 24858643; 24893874
• PubChem CID: 172; 439423
• CHEBI ID: 17759
• Chemspider ID: 388534
• MeSH Name: 7-dehydrocholesterol
• Unique Ingredient Identifier: BK1IU07GKF
• Wikipedia Title: 7-Dehydrocholesterol

CALCULATED PROPERTIES

• Acid pKa: 18.270805
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.7073097
• LogD (pH = 7.4): 6.7073097
• Log P: 6.7073097
• Molar Refractivity: 121.4665 cm^3
• Polarizability: 47.743767 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Light Yellow Solid
• Melting Point: 129-131°C; 142-151 °C; 148-152 °C(lit.)
• Optical Rotation: [α]20/D -116±6°, c = 1% in chloroform; [α]22/D -114°, c = 1 in chloroform

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85%; ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C27H44O

DETAILS

MP Biomedicals - 05205178

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D4429

Biochem/physiol Actions
Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.
Linkage
Do not confuse with dihydrocholesterol.
包装
1, 5 g in glass bottle
Sealed ampule

Sigma Aldrich - 30800

Biochem/physiol Actions
Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.

Sigma Aldrich - 456209

Biochem/physiol Actions
Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.

Toronto Research Chemicals - D229455

A vitamin precursor.