(1S,3E)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

• ChemBase ID: 54
• Molecular Formular: C27H44O
• Molecular Mass: 384.63766
• Monoisotopic Mass: 384.33921603
• SMILES: O[C@@H]1CC(=CC=C2[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(C)C)C)(CCC2)C)C(=C)CC1
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCCC2=CC=C1C[C@@H](O)CCC1=C)C)C
• InChI: InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/t21-,24+,25-,26+,27-/m1/s1
• InChIKey: QYSXJUFSXHHAJI-RWDMXNMGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3E)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol; (1S)-3-{2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol; (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• IUPAC Traditional name: delta-D; (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol; cholecalciferol; vitamin D3
• Brand Name: Calciol; Delsterol; Delta-D; Deparal; Ebivit; Micro-Dee; Oleovitamin D3; Provitamin D3; Provitamine; Provitina; Ricketon; Trivitan; Vigantol; Vigorsan
• Synonyms: Vitamin D3; (1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-Dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylenecyclohexanol; (3β,5E,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol; (E,E)-9,10-Secocholesta-5,7,10(19)-trien-3β-ol; 5,6-trans-Cholecalciferol; trans-Vitamin D3; 5,6-trans-Vitamin D3; (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol; Duphafral D3 1000; Delsterol; Deparal; Ebivit; Oleovitamin D3; Provitina; Ricketon; Vi-De3; Videkhol; Vigorsan; Vitinc Dan-Dee-3; Vitamin D3; Colecalciferol; (+)-Vitamin D3; 7-Dehydrocholesterol activated; Activated 7-dehydrocholesterol; Calciol; Cholecalciferolum; Cholecalciferol solution; Vitamin D3 solution; Vitamin D3; CC; Cholecalciferol, D3; Colecalciferol; Cholecalciferol; Cholecalciferol; Cholecalciferol; Cholecalciferol (D3); 维生素D3; 胆钙化醇; 胆钙化醇 溶液; (+)-维生素 D3; 活化7-脱氢胆固醇; 活化7-脱氢胆甾醇; 胆骨化醇; 胆钙化醇; 胆钙化固醇（维生素 D3）

Database IDs

• CAS Number: 67-97-0; 22350-41-0
• EC Number: 200-578-6; 200-673-2
• MDL Number: MFCD00078131
• Beilstein Number: 2339331
• Merck Index: 1410019
• PubChem SID: 24893197; 160963517; 24871395; 24893192; 24889192; 24892404
• PubChem CID: 6221

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.384342
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.1254606
• LogD (pH = 7.4): 7.1254606
• Log P: 7.1254606
• Molar Refractivity: 123.2245 cm^3
• Polarizability: 48.251457 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 7.98
• LOG S: -6.01
• Solubility (Water): 3.80e-04 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethyl Acetate; Insoluble; Methanol
• Apperance: White Solid; White to Off-White Solid
• Melting Point: 67-73°C; 82-84°C; 83-86 °C; 83-86 °C(lit.); 83-87°C
• Flash Point: 14 °C; 57.2 °F
• Optical Rotation: [α]20/D +109±3°, c = 2% in ethanol; +108 (c=0.8 in ethanol)
• Hydrophobicity(logP): 7.5

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer; Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Air & Light Sensitive
• RTECS: VS2900000
• European Hazard Symbols: Flammable (F); Highly toxic (T+)
• UN Number: 2811; UN2811
• German water hazard class: 1; 2
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 11; 24/25-26-48/25
• Safety Statements: 1/2-28-36/37-45; 28-36/37-45; 7-16
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H301-H311-H330-H372
• GHS Precautionary statements: P210; P260-P280-P284-P301 + P310-P310; P260-P301+P310-P304+P340-P320-P330-P361-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Mechanism of Action: Calcium homeostasis regulator

Product Information

• Purity: ≥98% (HPLC); ≥99.0% (sum of enantiomers, HPLC); 98% (CP); 99%
• Concentration: 100 μg/mL in ethanol
• Grade: analytical standard; Ph Eur
• Packaging: ampule of 100 mg; pkg of 250 mg
• Suitability: meets USP testing specifications
• Biological Source: Constit. of fish-liver oil, esp. tuna oil. Dietary supplement
• Shelf Life: 3 mo. at -20 °C (Please inquire with isosales@sial.com for a batch specific expiration date.)
• Application(s): Antirachitic vitamin with approx. the same potency as vitamin D 2 in humans
• Feature: standard type fat soluble vitamin
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C27H44O

DETAILS

DrugBank - DB00169

• Drug Groups: approved; nutraceutical
• Description: Derivative of 7-dehydroxycholesterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from ergocalciferol in having a single bond between C22 and C23 and lacking a methyl group at C24. [PubChem]
• Indication: For the treatment of vitamin D deficiency or insufficiency, refractory rickets (vitamin D resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. Also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis.
• Pharmacology: Cholecalciferol (vitamin D3) is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of Vitamin A. The classical manifestations of vitamin D deficiency is rickets, which is seen in children and results in bony deformaties including bowed long bones. Deficiency in adults leads to the disease osteomalacia. Both rickets and osteomalacia reflect impaired mineralization of newly synthesized bone matrix, and usually result from a combination of inadequate exposure to sunlight and decreased dietary intake of vitamin D. Common causes of vitamin D deficiency include genetic defects in the vitamin D receptor, severe liver or kidney disease, and insufficient exposure to sunlight. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma.
• Toxicity: Hypercalcemia - Early symptoms of hypercalcemia, include nausea and vomiting, weakness, headache, somnolence, dry mouth, constipation, metallic taste, muscle pain and bone pain. Late symptoms and signs of hypercalcemia, include polyuria, polydipsia, anorexia, weight loss, nocturia, conjunctivitis, pancreatitis, photophobia, rhinorrhea, pruritis, hyperthermia, decreased libido, elevated BUN, albuminuria, hypercholesterolemia, elevated ALT (SGPT) and AST (SGOT), ectopic calcification, nephrocalcinosis, hypertension and cardiac arrhythmias.
• Affected Organisms: Humans and other mammals
• Biotransformation: Within the liver, cholecalciferal is hydroxylated to calcidiol (25-hydroxycholecalciferol) by the enzyme 25-hydroxylase. Within the kidney, calcidiol serves as a substrate for 1-alpha-hydroxylase, yielding calcitriol (1,25-dihydroxycholecalciferol), the biologically active form of vitamin D3.
• Absorption: Readily absorbed
• Half Life: Several weeks
• Protein Binding: 50% to 80%
• References: Armas LA, Hollis BW, Heaney RP: Vitamin D2 is much less effective than vitamin D3 in humans. J Clin Endocrinol Metab. 2004 Nov;89(11):5387-91. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - C9756

包装
1, 5 g in glass bottle
Biochem/physiol Actions
维生素 D 借以发挥作用的受体是配体依赖性转录因子超家族的成员。调控正常细胞和癌细胞的增殖和分化。对乳腺癌、结肠癌和前列腺癌细胞具有抗增殖和抗转移作用。肠和骨骼中的活化维生素 D 受体维持着钙的吸收和平衡。

Sigma Aldrich - 95230

Other Notes
Review: Vitamin D: Recent advances1
Unit Definition
1 U corresponds to 1 international U according to commentary-DAB, 8th issue, 38 (1981)
Biochem/physiol Actions
Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor superfamily. Modulates the proliferation and differentiation of both normal and cancer cells. Has antiproliferative and antimetastatic effects on breast, colon, and prostate cancer cells. Activated vitamin D receptors in intestine and bone maintain calcium absorbance and homeostasis.

Sigma Aldrich - 89193

Biochem/physiol Actions
Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor superfamily. Modulates the proliferation and differentiation of both normal and cancer cells. Has antiproliferative and antimetastatic effects on breast, colon, and prostate cancer cells. Activated vitamin D receptors in intestine and bone maintain calcium absorbance and homeostasis.

Sigma Aldrich - C1357

Biochem/physiol Actions
维生素 D 借以发挥作用的受体是配体依赖性转录因子超家族的成员。调控正常细胞和癌细胞的增殖和分化。对乳腺癌、结肠癌和前列腺癌细胞具有抗增殖和抗转移作用。肠和骨骼中的活化维生素 D 受体维持着钙的吸收和平衡。

Sigma Aldrich - C9774

包装
Packaged in flame-sealed ampules under Argon
Biochem/physiol Actions
维生素 D 借以发挥作用的受体是配体依赖性转录因子超家族的成员。调控正常细胞和癌细胞的增殖和分化。对乳腺癌、结肠癌和前列腺癌细胞具有抗增殖和抗转移作用。肠和骨骼中的活化维生素 D 受体维持着钙的吸收和平衡。

Sigma Aldrich - 47763

Biochem/physiol Actions
Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor superfamily. Modulates the proliferation and differentiation of both normal and cancer cells. Has antiproliferative and antimetastatic effects on breast, colon, and prostate cancer cells. Activated vitamin D receptors in intestine and bone maintain calcium absorbance and homeostasis.

Toronto Research Chemicals - V676045

The vitamin that mediates intestinal calcium absorbtion, bone calcium metabolism and probably, muscle activity. Occurs in and is isolated from fish liver oils. Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor

Toronto Research Chemicals - V676065

5,6-trans-Vitamin D3 is the major photoisomer of Vitamin D3 analog, as an impurity.

REFERENCES

• Armas LA, Hollis BW, Heaney RP: Vitamin D2 is much less effective than vitamin D3 in humans. J Clin Endocrinol Metab. 2004 Nov;89(11):5387-91. Pubmed
• Haussler, R., et al.: J. Biol. Chem., 247, 2328 (1972)
• Holick, M.F., Rec. Res. Canc. Res., 164, 3 (1972)
• Palmer, H.G., et al.: Cancer Res., 63, 7799 (1972)
• Welsh, J., et al.: J. Nutr., 133, 2425S (1972)
• Bikle, D., et al.: Biochemistry, 25, 1545 (1986)
• Webb, A., et al.: J. Clin. Endocrinol. Metab., 68, 882 (1986)
• Baran, D., et al.: J. Cell Biochem., 50, 124 (1986)
• Tian, X., et al.: J. Biol. Chem., 268, 14888 (1986)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1049D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 570C, (nmr)
• Inhoffen, M. et al., Angew. Chem., 1960, 72, 875, (rev)
• Haussler, M.S. et al., J. Biol. Chem., 1972, 247, 2328, (rev)
• Borle, A.B., Annu. Rev. Physiol., 1974, 36, 361, (rev, metab)
• Wing, R.M. et al., J.A.C.S., 1975, 97, 4980, (pmr, conformn)
• Okamura, W.H. et al., Tet. Lett., 1976, 4807, (ms)
• Lythgoe, B. et al., Tet. Lett., 1977, 3685, (synth)
• Fraser, D.R., Br. Med. Bull., 1981, 37, 37, (rev, metab)
• Pure Appl. Chem., 1982, 54, 1511, (nomencl)
• Koshy, K.T. et al., Anal. Profiles Drug Subst., 1984, 13, 655, (rev)
• Wilson, S.R. et al., Tet. Lett., 1984, 25, 3147, (synth)
• Nemoto, H. et al., Heterocycles, 1985, 23, 567, (synth)
• Nemoto, H. et al., J.O.C., 1986, 51, 5311, (synth)
• Coldwell, R.D. et al., Steroids, 1990, 55, 418, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1058
• Zhu, G.-D. et al., Chem. Rev., 1995, 95, 1877, (rev, synth)
• Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 2935-2937, (props, use)
• Jankowski, P. et al., Tetrahedron, 1998, 54, 12071-12150, (rev, synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMC750; HJV000