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22350-41-0 molecular structure
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(1S)-3-{2-[(1R,3aS,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 and InChIs

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

Cite this record

CBID:54 http://www.chembase.cn/molecule-54.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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
(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
IUPAC Traditional name
cholecalciferol
vitamin D3
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
Brand Name
Calciol
Delsterol
Delta-D
Deparal
Ebivit
Micro-Dee
Oleovitamin D3
Provitamin D3
Provitamine
Provitina
Ricketon
Trivitan
Vigantol
Vigorsan
Synonyms
Vitamin D3
CC
Cholecalciferol, D3
Colecalciferol
Cholecalciferol
Cholecalciferol
Cholecalciferol solution
Vitamin D3 solution
(+)-Vitamin D3
7-Dehydrocholesterol activated
Activated 7-dehydrocholesterol
Calciol
Cholecalciferolum
Cholecalciferol
Cholecalciferol (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
Colecalciferol
Ebivit
Oleovitamin D3
Provitina
Ricketon
Vi-De3
Videkhol
Vigorsan
Vitinc Dan-Dee-3
Vitamin D3
Vitamin D3
(+)-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
胆钙化醇 溶液
胆钙化固醇(维生素 D3)
胆钙化醇
维生素D3
CAS Number
22350-41-0
67-97-0
EC Number
200-578-6
200-673-2
MDL Number
MFCD00078131
Beilstein Number
2339331
Merck Index
1410019
PubChem SID
24892404
24893197
160963517
24871395
24889192
24893192
PubChem CID
6221

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 18.384342  H Acceptors
H Donor LogD (pH = 5.5) 7.1254606 
LogD (pH = 7.4) 7.1254606  Log P 7.1254606 
Molar Refractivity 123.2245 cm3 Polarizability 48.251457 Å3
Polar Surface Area 20.23 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 7.98  LOG S -6.01 
Solubility (Water) 3.80e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Acetone expand Show data source
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Insoluble expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
67-73°C expand Show data source
82-84°C expand Show data source
83-86 °C expand Show data source
83-86 °C(lit.) expand Show data source
83-87°C expand Show data source
Flash Point
14 °C expand Show data source
57.2 °F expand Show data source
Optical Rotation
[α]20/D +109±3°, c = 2% in ethanol expand Show data source
+108 (c=0.8 in ethanol) expand Show data source
Hydrophobicity(logP)
7.5 expand Show data source
Storage Condition
Amber Vial, -20°C Freezer expand Show data source
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
Storage Warning
Air & Light Sensitive expand Show data source
RTECS
VS2900000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
UN2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
2 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Risk Statements
11 expand Show data source
24/25-26-48/25 expand Show data source
Safety Statements
1/2-28-36/37-45 expand Show data source
28-36/37-45 expand Show data source
7-16 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225 expand Show data source
H301-H311-H330-H372 expand Show data source
GHS Precautionary statements
P210 expand Show data source
P260-P280-P284-P301 + P310-P310 expand Show data source
P260-P301+P310-P304+P340-P320-P330-P361-P405-P501A expand Show data source
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 expand Show data source
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Mechanism of Action
Calcium homeostasis regulator expand Show data source
Purity
≥98% (HPLC) expand Show data source
≥99.0% (sum of enantiomers, HPLC) expand Show data source
98% (CP) expand Show data source
99% expand Show data source
Concentration
100 μg/mL in ethanol expand Show data source
Grade
analytical standard expand Show data source
Ph Eur expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
ampule of 100 mg expand Show data source
pkg of 250 mg expand Show data source
Suitability
meets USP testing specifications expand Show data source
Biological Source
Constit. of fish-liver oil, esp. tuna oil. Dietary supplement expand Show data source
Shelf Life
3 mo. at -20 °C (Please inquire with isosales@sial.com for a batch specific expiration date.) expand Show data source
Application(s)
Antirachitic vitamin with approx. the same potency as vitamin D 2 in humans expand Show data source
Feature
standard type fat soluble vitamin expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Empirical Formula (Hill Notation)
C27H44O expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC DrugBank DrugBank
Sigma Aldrich - C9774 external link
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 - 95230 external link
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 - 47763 external link
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 external link
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 external link
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 - C9756 external link
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。
Toronto Research Chemicals - V676045 external link
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 external link
5,6-trans-Vitamin D3 is the major photoisomer of Vitamin D3 analog, as an impurity.
DrugBank - DB00169 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • 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)
  • • 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)
  • • 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
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