5226-01-7

Basic information

• Product Name: Lumisterol 3
• Synonyms: Lumisterol 3;7-dien-3-ol, 3.beta.,9.beta.,10.alpha.-Cholesta-5;(9β,10α)-Cholesta-5,7-dien-3β-ol;(3β,9β,10α)-Cholesta-5,7-dien-3-ol;Cholecalciferol EP Impurity C;(3S,9R,10S,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;Cholecalciferol impurity C
• CAS NO: 5226-01-7
• Molecular Formula: C27H44O
• Molecular Weight: 384.64
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 5226-01-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 493.7°Cat760mmHg
• Flash Point: 212.3°C
• Appearance: /
• Density: 1g/cm³
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
• PKA: 14.91±0.70(Predicted)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: Lumisterol 3(CAS DataBase Reference)
• NIST Chemistry Reference: Lumisterol 3(5226-01-7)
• EPA Substance Registry System: Lumisterol 3(5226-01-7)

Safety Data

• Hazardous Substances Data: 5226-01-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 5226-01-7 differently. You can refer to the following data:
1. Lumisterol3 is an isomer of Vitamin D3 (V676045). Lumisterol3 is used in the preparation of vitamin D analogs.
2. Lumisterol 3 (Cholecalciferol EP Impurity A) is an isomer of Vitamin D3 (V676045). Lumisterol 3 is used in the preparation of vitamin D analogs.

Upstream product

• 1059-86-5 cholesta-5,7-dien-3β-yl acetate 
• 434-16-2 7-dehydrocholesterol 
• 1173-13-3 previtamin D₃ 
• 1173-13-3 previtamin D₃ 

Downstream Products

• 1173-13-3 tachysterol₃ 
• 434-16-2 7-dehydrocholesterol 
• 1173-13-3 previtamin D₃ 
• 124580-51-4 3.5-dinitro-benzoic acid-(9β.10α-cholestadien-(5.7)-yl-(3β)-ester) 

Relevant articles and documents

Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3β, 17α, 20-triol and their bioactivity in melanoma cells

Pregna-5,7-dienes and their hydroxylated derivatives can be formed in vivo when there is a deficiency in 7-dehydrocholesterol (7-DHC) Δ-reductase function, e.g., Smith-Lemli-Opitz syndrome (SLOS). Ultraviolet B (UVB) radiation induces photoconversion of 7-DHC to vitamin D3, lumisterol3 and tachysterol3. Two epimers (20R and 20S) of pregna-5,7-diene-3β,17α,20-triol (4R and 4S, respectively) were synthesized and their UVB photo-conversion products identified as corresponding 9,10-secosteroids with vitamin D-like and tachysterol-like structures, and 5,7-dienes with inverted configuration at C-9 and C-10 (lumisterol-like). The number and character of the products and the dynamics of the process were dependent on the UVB dose. At high UVB doses, the formation of multiple oxidized derivatives of the primary products, and the formation of 5,7,9(11)-triene, were observed. The production of vitamin D-like, tachysterol-like and lumisterol-like derivatives was also observed in human skin treated with 4R and 4S, and subjected to UV irradiation, as shown by RP-HPLC. Newly synthesized compounds inhibited melanoma growth in dose dependent manner, and some of them showed equal or higher potency than 1,25(OH)2D3. In summary, we have characterized for the first time the products of UV induced conversion of pregna-5,7-diene-3β,17α,20-triols and documented that the newly synthesized compounds have antiproliferative properties against melanoma cells.

Novel Photosensitizers for the E/Z-Isomerization of Trienes. Part 1. Synthesis and Application

Uranine and its thioxanthene and selenoxanthene analogues, as well as the disodium salts of o-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzenesulphonic acid and its thioxanthene and selenoxanthene analogues, show different photosensitizer properties in the E/Z-isomerization of trienes.This has been verified by applying them to the technically useful conversion of tachysterol into previtamin D.The synthesis of the novel photosensitizers with thioxanthene and selenoxanthene moieties are also described.

Separation of photoisomers of provitamin D3 by chromatographic methods

-