474-69-1

Basic information

• Product Name: 9-beta,10-alpha-ergosta-5,7,22-trien-3-beta-ol
• Synonyms: 9-beta,10-alpha-ergosta-5,7,22-trien-3-beta-ol;Ergosta-5,7,22-trien-3-ol, (3.beta.,9.beta.,10.alpha.,22E)-;(9β,10α,22E)-Ergosta-5,7,22-trien-3β-ol;Einecs 207-487-0;(3beta,9beta,10alpha,22E)-Ergosta-5,7,22-trien-3-ol
• CAS NO: 474-69-1
• Molecular Formula: C28H44O
• Molecular Weight: 396.64836
• EINECS: 207-487-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 474-69-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 118-120℃ (ethanol )
• Boiling Point: 460.3°C (rough estimate)
• Flash Point: 216.275 °C
• Appearance: /
• Density: 1.00±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3.7E-12mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• PKA: 14.91±0.70(Predicted)
• CAS DataBase Reference: 9-beta,10-alpha-ergosta-5,7,22-trien-3-beta-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 9-beta,10-alpha-ergosta-5,7,22-trien-3-beta-ol(474-69-1)
• EPA Substance Registry System: 9-beta,10-alpha-ergosta-5,7,22-trien-3-beta-ol(474-69-1)

Safety Data

• Hazardous Substances Data: 474-69-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 474-69-1 differently. You can refer to the following data:
1. Differs from Ergosterol by spatial arrangement volving the methyl group at C10. 9-beta,10-alpha-ergosta-5,7,22-trien-3-beta-ol is used in the preparation of vitamin D series.
2. C10 isomer of Ergosterol (E599240). Used in the preparation of vitamin D series.

InChI:InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26+,27+,28+/m0/s1

Synthetic route

Ergosterol (57-87-4) → previtamin D2 (21307-05-1) + lumisterol (474-69-1) + tachysterol (115-61-7)

Conditions	Yield
Product distribution; Irradiation;	A 79.8% B 9.8% C 1.5%

Ergosterol (57-87-4) → lumisterol (474-69-1)

Conditions	Yield
With 9-acetylanthracene In tetrahydrofuran at 10 - 15℃; for 8.33333h; Time; Reagent/catalyst; UV-irradiation;	29%
With ethanol; benzene Irradiation.UV-Licht (λ: > 280 mμ); Isolierung aus der erhaltenen Verbindung mit Ergocalciferol ueber das O-Acetyl-Derivat oder das O-<3.5-Dinitro-benzoyl>-Derivat;
In ethanol Irradiation;

diethyl ether (60-29-7) + Ergosterol (57-87-4) → Calciferol (50-14-6) + lumisterol (474-69-1) + tachysterol (115-61-7)

Conditions	Yield
mit UV-Licht unter Kuehlung bei Luftausschluss.Irradiation;

diethyl ether (60-29-7) + previtamin D2 (21307-05-1) → Ergosterol (57-87-4) + lumisterol (474-69-1) + tachysterol (115-61-7)

Conditions	Yield
at 0℃; UV-Licht.Irradiation;

diethyl ether (60-29-7) + tachysterol (115-61-7) → previtamin D2 (21307-05-1) + lumisterol (474-69-1)

Conditions	Yield
at 20℃; UV-Licht.Irradiation;

previtamin D2 (21307-05-1) → lumisterol (474-69-1)

tachysterol (115-61-7) → lumisterol (474-69-1)

ethanol (64-17-5) + Ergosterol (57-87-4) + benzene (71-43-2) → Calciferol (50-14-6) + lumisterol (474-69-1) + tachysterol (115-61-7)

Conditions	Yield
mit UV-Licht unter Kuehlung bei Luftausschluss.Irradiation;

Ergosterol (57-87-4) + benzene (71-43-2) → Calciferol (50-14-6) + lumisterol (474-69-1) + tachysterol (115-61-7)

Conditions	Yield
mit UV-Licht unter Kuehlung bei Luftausschluss.Irradiation;

(10S)-3c-Hydroxy-10r.13t-dimethyl-17t-((1R:4R)-1.4.5-trimethyl-hexen-(2t)-yl)-(9tH.14cH)-Δ5.7-dodecahydro-1H-cyclopenta[a]phenanthren (6538-06-3) + aluminum isopropoxide (555-31-7) + benzene (71-43-2) → lumisterol (474-69-1)

7-dehydrocholesterol (434-16-2) → previtamin D2 (21307-05-1) + lumisterol (474-69-1) + Tachysterol (115-61-7, 21307-05-1, 24945-48-0, 137174-34-6)

Conditions	Yield
Product distribution; Irradiation; effect of use var. wave-length of irradiation;

Ergosterol (57-87-4) → previtamin D2 (21307-05-1) + lumisterol (474-69-1) + Tachysterol (115-61-7, 21307-05-1, 24945-48-0, 137174-34-6)

Conditions	Yield
In n-heptane at 25℃; Product distribution; Quantum yield; Irradiation; var. reaction temperatures, var. wavelengths;

Ergosterol (57-87-4) → Calciferol (50-14-6) + previtamin D2 (21307-05-1) + lumisterol (474-69-1) + tachysterol (115-61-7)

Conditions	Yield
With var. irradiation time; the influence of sunlamp emission spectrum on the course of the reaction In ethanol Product distribution; Irradiation;

Ergosterol (57-87-4) → lumisterol (474-69-1) + Previtamin D2

Conditions	Yield
In ethanol Isomerization; UV-irradiation;

tetrachloromethane (56-23-5) + lumisterol (474-69-1) + aluminum isopropoxide (555-31-7) → (10S)-3c-Hydroxy-10r.13t-dimethyl-17t-((1R:4R)-1.4.5-trimethyl-hexen-(2t)-yl)-(9tH.14cH)-Δ5.7-dodecahydro-1H-cyclopenta[a]phenanthren (6538-06-3)

Perbenzoic acid (93-59-4) + lumisterol (474-69-1) → benzoic acid-(3β.5-dihydroxy-5β-lumistadien-(7.22t)-yl-(6β)-ester) (10180-50-4)

Conditions	Yield
With chloroform
With benzene

lumisterol (474-69-1) → 3β-(4-iodo-3-nitro-benzoyloxy)-lumista-5,7,22t-triene (60426-98-4)

lumisterol (474-69-1) → lumistatetraene-(3.5.7.22t) (75678-55-6)

Conditions	Yield
With pyridine; trichlorophosphate

lumisterol (474-69-1) → (10S)-3c-Hydroxy-10r.13t-dimethyl-17t-((1R:4R)-1.4.5-trimethyl-hexen-(2t)-yl)-(9tH.14cH)-Δ5.7-dodecahydro-1H-cyclopenta[a]phenanthren (6538-06-3)

Conditions	Yield
With aluminum isopropoxide; xylene

lumisterol (474-69-1) → 5β-lumistadien-(7.22t)-ol-(3β) (1105-11-9, 1105-12-0, 2465-11-4, 5035-32-5, 17608-76-3, 26596-33-8, 27245-94-9, 27245-95-0, 41388-21-0, 50364-22-2, 54482-53-0, 60426-59-7, 96391-64-9, 96391-66-1, 96996-85-9, 96996-86-0, 116296-50-5)

Conditions	Yield
With ethanol; sodium

lumisterol (474-69-1) → suprasterol2-I (562-71-0, 42763-68-8) + 6β,8β;7α,19-dicyclo-9,10-seco-ergosta-5(10),22t-dien-3β-ol (562-71-0, 42763-68-8)

Conditions	Yield
With ethanol Irradiation.UV-Licht (Quecksilber-Lampe) unter Luftausschluss;
With ethanol Irradiation.UV-Licht (Quecksilber-Lampe);

lumisterol (474-69-1) → 5β-lumistatrien-(8.14.22t)-ol-(3β) (3571-56-0)

Conditions	Yield
With chloroform at -10℃; Einleiten von HCl;

lumisterol (474-69-1) → lumista-4,7,22t-trien-3-one (3957-32-2)

Conditions	Yield
With aluminum tri-tert-butoxide; acetone; benzene

lumisterol (474-69-1) → lumista-4,6,8(14),22t-tetraen-3-one (19254-69-4, 142796-29-0)

Conditions	Yield
With aluminum tri-tert-butoxide; p-benzoquinone

Calciferol (50-14-6) + lumisterol (474-69-1) + acetic anhydride (108-24-7) → isopyrocalcyferyl acetate (3957-39-9)

lumisterol (474-69-1) + p-toluenesulfonyl chloride (98-59-9) → lumistatetraene-(3.5.7.22t) (75678-55-6)

Conditions	Yield
With pyridine at 100℃;

lumisterol (474-69-1) + benzene (71-43-2) → tachysterol (115-61-7)

Conditions	Yield
UV-Licht (Magnesium-Funken).Irradiation;

Upstream product

• 60-29-7 diethyl ether 
• 57-87-4 Ergosterol 
• 21307-05-1 previtamin D₂ 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 434-16-2 7-dehydrocholesterol 
• 70005-45-7 ergosta-5,7,22-trien-3β-ol 
• 6411-40-1 3-acetoxy-3,5,7,22-ergosta-tetraene 
• 3946-26-7 (20S)-20-formyl-pregna-4,6-dien-3-one 
• 3986-89-8 (20S)-3-oxopregn-4-ene-20-carboxaldehyde 
• 40736-33-2 (20S)-20-hydroxymethylpregn-4-en-3-one 
• 1108-03-8 ergosta-5,7,22-trien-3β-yl acetate 
• 81139-11-9 C₃₈H₅₂N₂O₃ 
• 81139-13-1 C₃₆H₄₈N₂O₃ 

Downstream Products

• 10180-50-4 benzoic acid-(3β.5-dihydroxy-5β-lumistadien-(7.22t)-yl-(6β)-ester) 
• 50-14-6 Calciferol 
• 21307-05-1 previtamin D₂ 
• 6034-23-7 3β-allophanoyloxy-lumistatriene-(5.7.22t) 
• 520-91-2 Vitamin D₁ 
• 115-61-7 tachysterol 
• 705926-28-9 (22E)-3β-hydroxyergosta-8(14),22-dien-15-one 
• 55401-50-8 (3S,5S,8R,9S,10S,13R,17R)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 20817-91-8 lumista-4,6,8⁽¹⁴⁾,22t-tetraen-3-one-(2,4-dinitro-phenylhydrazone) 
• 4712-11-2 O-(3.5-dinitro-benzoyl)-ergocalciferol 
• 1449-60-1 5β-lumistadien-(7.22t)-yl-(3β)-acetate 
• 1449-60-1 5β-lumistadien-(7.22t)-yl-(3α)-acetate 
• 1449-60-1 Acetic acid (3S,5S,9R,10S,13R,17R)-10,13-dimethyl-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 6113-02-6 3β-(3,5-dinitro-benzoyloxy)-lumista-5,7,22t-triene 

Relevant articles and documents

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ROUTES TO OPTIMIZATION OF PREVITAMIN D PHOTOSYNTHESIS USING IRRADIATION BY A SUNLAMP

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