566-27-8

Basic information

• Product Name: 7BETA-HYDROXYCHOLESTEROL
• Synonyms: 7BETA-HYDROXYCHOLESTEROL;3BETA,7BETA-DIHYDROXY-5-CHOLESTENE;5-CHOLESTEN-3-BETA, 7-BETA-DIOL;5-CHOLESTENE-3BETA,7BETA-DIOL;7B-hydroxycholesterol;cholest-5-ene-3-beta,7-beta-diol;7|beta|-Hydroxycholesterol (not deuterated);5-cholestene-3β,7β-diol
• CAS NO: 566-27-8
• Molecular Formula: C27H46O2
• Molecular Weight: 402.65
• Product Categories: Hydroxycholesterol;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 566-27-8.mol
• Article Data: 32

Chemical Properties

• Melting Point: 165-167?C
• Boiling Point: 515.3 ºC at 760 mmHg
• Flash Point: 214.7 ºC
• Appearance: /
• Density: 1.03 g/cm³
• Vapor Pressure: 8.93E-13mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 14.11±0.70(Predicted)
• CAS DataBase Reference: 7BETA-HYDROXYCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 7BETA-HYDROXYCHOLESTEROL(566-27-8)
• EPA Substance Registry System: 7BETA-HYDROXYCHOLESTEROL(566-27-8)

Safety Data

• Safety Statements: 22-26
• Hazardous Substances Data: 566-27-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A metabolite of Cholesterol. Its membrane organizing properties could have implications in Altzheimer’s disease.

InChI:InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1

Synthetic route

3β,7β-cholest-5-ene-3,7-diol-3-benzoate (17974-80-0) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With sodium carbonate In methanol; water for 0.5h; Heating;	100%
With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran for 48h; Heating;	90 mg

3β-acetoxy-7β-hydroxycholest-5-ene (17974-77-5) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With water; sodium hydroxide In ethanol; dichloromethane at 20℃; for 2h;	95%
With sodium carbonate In methanol; water at 25℃; Inert atmosphere;

cholest-5-ene-3β,7β-diol diacetate (18099-24-6) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; Deacetylation;	87%

7-ketocholesteryl acetate (809-51-8) → (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 65℃; for 2h;	A 80% B n/a
With aluminum isopropoxide; isopropyl alcohol Behandeln der Reaktionsloesung mit wss. KOH bei Raumtemperatur;
With lithium aluminium tetrahydride

7-Oxocholesterol (566-28-9) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 2h;	79%
With sodium tetrahydroborate; cerium(III) chloride In tetrahydrofuran; methanol for 0.166667h; Ambient temperature;	78%
With sodium tetrahydroborate; cerium(III) chloride In tetrahydrofuran; methanol at 20℃; for 1h;	75%
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at 0 - 20℃; for 4h; Inert atmosphere;	58%
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 0 °C 2: 1) 1M L-Selectride, 2) 6 M aq. NaOH, 30percent H2O2 / 1) THF, -78 deg C, 5 h, 2) THF, H2O, r.t., 1 h 3: 90 mg / nBu4NBr, 0.5 M aq. NaOH / tetrahydrofuran / 48 h / Heating View Scheme

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In dichloromethane at 23℃; for 48h; Catalytic behavior; Time; Temperature; chemoselective reaction;	A 53% B 15%

tert.-butylhydroperoxide (75-91-2) + cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + 3β-hydroxycholest-5-ene-7α-hydroperoxide (36871-91-7, 75671-16-8, 75671-17-9, 86900-29-0, 2846-29-9) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 7β-hydroperoxy-3β-hydroxycholest-5-ene (36871-91-7)

Conditions	Yield
Rh2(cap)4 In dichloromethane at 25℃; for 15h; Allylic oxidation;	A 30% B 10% C 12% D 3% E 4%

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + 3β-hydroxycholest-5-ene-7α-hydroperoxide (36871-91-7, 75671-16-8, 75671-17-9, 86900-29-0, 2846-29-9) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 7β-hydroperoxy-3β-hydroxycholest-5-ene (36871-91-7)

Conditions	Yield
With tert.-butylhydroperoxide; [Rh2(cap)4*2CH3CN] In water; 1,2-dichloro-ethane at 25℃; for 15h;	A 30% B 10% C 12% D 3% E 4%

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + cholest-5-en-3β,7β-diol (566-27-8) + 5beta,6beta-Epoxycholestanol (2953-38-0, 4025-59-6, 24116-45-8, 55700-78-2, 75764-48-6, 97100-48-6, 114246-94-5, 134356-45-9, 1250-95-9) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Conditions	Yield
at 150℃; Further byproducts given;	A 21.9% B 13% C 7.4% D 10.8%
at 150℃; Further byproducts given;	A 21.9% B 13% C 7.4% D 10.8%
at 150℃; for 1h;

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + 25-hydroxychlolesterol (2140-46-7) + cholest-5-en-3β,7β-diol (566-27-8) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Conditions	Yield
at 150℃; Further byproducts given;	A 21.9% B 2.3% C 13% D 10.8%

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Conditions	Yield
at 150℃; Further byproducts given;	A 21.9% B 4% C 13% D 10.8%

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + cholest-5-en-3β,7β-diol (566-27-8) + 22(R)-Hydroxycholesterol (17954-98-2) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Conditions	Yield
at 150℃; Further byproducts given;	A 21.9% B 13% C 0.6% D 10.8%

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + cholest-5-en-3β,7β-diol (566-27-8) + 22-(S)-hydroxycholesterol (17711-16-9, 17954-98-2, 22348-64-7, 59532-44-4, 59532-45-5) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Conditions	Yield
at 150℃; Further byproducts given;	A 21.9% B 13% C 0.3% D 10.8%

cholesterol (57-88-5) → cholest-5-en-3β,7β-diol (566-27-8)

7-ketocholesteryl acetate (809-51-8) + aluminum isopropoxide (555-31-7) + isopropyl alcohol (67-63-0) → (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
anschliessenden Behandeln mit wss.KOH;
anschliessenden Behandeln mit wss.KOH;

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + cholestanetriol (1253-84-5) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 3β-hydroxycholest-5-ene-7-hydroperoxide (86900-29-0) + (6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol (55700-78-2)

Conditions	Yield
With egg lechitin; oxygen; tris(acetylacetonato)iron(III) In benzene at 40℃; for 24h; Product distribution; determination of fatty acid degradation, determination of stereoselectivity of epoxidation, inhibition of a radical scavenger in the oxidation, other temperature, other solvent, other catalyst;

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + cholestanetriol (1253-84-5) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 5beta,6beta-Epoxycholestanol (2953-38-0, 4025-59-6, 24116-45-8, 55700-78-2, 75764-48-6, 97100-48-6, 114246-94-5, 134356-45-9, 1250-95-9) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Conditions	Yield
With air at 150℃; for 24h; Product distribution; var. temperature, var. time;

cholesterol (57-88-5) → Cholest-5-en-3-one (601-54-7) + Cholest-4-en-3-one (601-57-0) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 5beta,6beta-Epoxycholestanol (2953-38-0, 4025-59-6, 24116-45-8, 55700-78-2, 75764-48-6, 97100-48-6, 114246-94-5, 134356-45-9, 1250-95-9) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Conditions	Yield
With tetrasodium 5,10,15,20-tetra(4-sulfophenyl)porphyrinatoiron(III); dihydrogen peroxide In 2,2,4-trimethylpentane; water for 12h; Product distribution; other sterols, other iron(III) porphyrins; var. water/surfactant ratio and pH; oxidation in AOT reversed micelles;

Cholesteryl acetate (604-35-3) → (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With tert.-butylhydroperoxide; lithium aluminium tetrahydride; potassium carbonate; chromium(0) hexacarbonyl Yield given. Multistep reaction. Yields of byproduct given;

5α-hydroperoxy-3β-benzoyloxycholest-6-ene (129238-78-4) → (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With potassium hydroxide; tributyltin methoxide; triphenylphosphine Multistep reaction;

7β-hydroperoxy-3β-hydroxycholest-5-ene (36871-91-7) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With triphenylphosphine In diethyl ether Ambient temperature;

3β-hydroxycholest-5-ene-7-hydroperoxide (86900-29-0) → (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With sodium tetrahydroborate In methanol; diethyl ether Reduction;	A n/a B 40 mg

cholesterol (57-88-5) + water (7732-18-5) + air + sodium-stearate → cholest-3,5-dien-7-one (567-72-6) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 3β-hydroxy-cholesten-(5)-one-(7)

Conditions	Yield
at 85℃; pH 8.5;

cholesterol (57-88-5) + water (7732-18-5) + oxygen + sodium-stearate → cholest-3,5-dien-7-one (567-72-6) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 3β-hydroxy-cholesten-(5)-one-(7)

Conditions	Yield
at 85℃; pH 8.5;

diethyl ether (60-29-7) + 7-ketocholesteryl acetate (809-51-8) + LiAlH4 → (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8)

cholesterol (57-88-5) → 3β,5α-dihydroxycholest-5-ene (34310-88-8) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
With lumiflavin; oxygen In acetonitrile for 4h; Product distribution; Further Variations:; Solvents; Reagents; reaction times; Irradiation;	A 12 mg B n/a C n/a

cholesterol (57-88-5) + ibu-guanosine → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / O2; N-hydroxyphthalamide; benzoyl peroxide / ethyl acetate; acetone / 72 h / 50 - 60 °C 2: 75 percent / CeCl3*H2O; NaBH4 / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

cholesterol (57-88-5) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: O2; hematoporphyrin / pyridine / 5 h / 10 °C / Irradiation 2: CHCl3 / 120 h / 20 °C 3: 40 mg / NaBH4 / methanol; diethyl ether View Scheme
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / Inert atmosphere 2: pyridinium chlorochromate / toluene / Inert atmosphere 3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 25 °C / Inert atmosphere 4: sodium carbonate / methanol; water / 25 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: pyridine / 37 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; methanol; water / 2 h / 20 °C 3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 4 h / 0 - 20 °C / Inert atmosphere View Scheme

cholesterol 5α-hydroperoxide (55529-60-7, 3328-25-4) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: CHCl3 / 120 h / 20 °C 2: 40 mg / NaBH4 / methanol; diethyl ether View Scheme

7-ketocholesteryl acetate (809-51-8) → cholest-5-en-3β,7β-diol (566-27-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LiALH4 / diethyl ether / 20 °C 1.2: 61 percent / pyridine / 1 h / 100 °C 2.1: 87 percent / NaOH / methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 25 °C / Inert atmosphere 2: sodium carbonate / methanol; water / 25 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: lithium hydroxide / tetrahydrofuran; methanol; water / 2 h / 20 °C 2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 4 h / 0 - 20 °C / Inert atmosphere View Scheme

cholest-5-en-3β,7β-diol (566-27-8) + Benzoyltriazole → 3β,7β-bis-benzoyloxy-cholest-5-ene (6038-38-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature;	95%

cholest-5-en-3β,7β-diol (566-27-8) → 7-Oxocholesterol (566-28-9)

Conditions	Yield
With 3,5-dimethyl-1H-pyrazole; pyridinium chlorochromate In dichloromethane at 2 - 3℃; for 0.5h;	89%

cholest-5-en-3β,7β-diol (566-27-8) → Δ4-7β-hydroxycholesterol (25876-54-4)

Conditions	Yield
With phosphate buffer pH 7; oxygen; (2-hydroxypropyl)-α-cyclodextrin at 20℃; for 24h; catalase, Brevibacterium sp. cholesterol oxidase E.C. 1.1.3.6;	85%
With catalase; cholesterol oxidase 1.) butyl acetate, 48 h; 2.) ethanol, oxalic acid, 30 min, 60 deg C; Yield given. Multistep reaction;
With buffer containing Triton-X 100; cetyltrimethylammonim bromide; cholesterol oxidase In cyclohexane; butan-1-ol Kinetics; further reaction conditions;
With recombinant Brevibacterium cholesterol oxidase In phosphate buffer; isopropyl alcohol at 25℃; for 12h; pH=7;

succinic acid anhydride (108-30-5) + cholest-5-en-3β,7β-diol (566-27-8) → cholest-5-ene-3β-7β-diyl dihemisuccinate (95615-70-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 24h; Inert atmosphere; Reflux;	83%

cholest-5-en-3β,7β-diol (566-27-8) → 5α-cholestane-3β,6α,7β-triol (202416-16-8)

Conditions	Yield
With sodium perborate tetrahydrate In tetrahydrofuran at 20℃; Inert atmosphere;	69%

(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid (2596-47-6, 147677-05-2, 34749-55-8) + cholest-5-en-3β,7β-diol (566-27-8) → 3-O-(4-acetoxyferuloyl)-7β-hydroxycholesterol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	42%

pyridine (110-86-1) + cholest-5-en-3β,7β-diol (566-27-8) + acetic anhydride (108-24-7) → 3β-acetoxy-7β-hydroxycholest-5-ene (17974-77-5)

Conditions	Yield
at 0℃;

cholest-5-en-3β,7β-diol (566-27-8) → 7-dehydrocholesterol (434-16-2)

cholest-5-en-3β,7β-diol (566-27-8) + oxalic acid (144-62-7) → 7-dehydrocholesterol (434-16-2)

Conditions	Yield
at 180 - 190℃;

cholest-5-en-3β,7β-diol (566-27-8) + acetic anhydride (108-24-7) → 3β-acetoxy-7β-hydroxycholest-5-ene (17974-77-5)

Conditions	Yield
With pyridine at 0℃;

cholest-5-en-3β,7β-diol (566-27-8) + acetic anhydride (108-24-7) → cholest-5-ene-3β,7β-diol diacetate (18099-24-6)

Conditions	Yield
With pyridine
With pyridine

cholest-5-en-3β,7β-diol (566-27-8) + benzoyl chloride (98-88-4) → 3β,7β-bis-benzoyloxy-cholest-5-ene (6038-38-6)

Conditions	Yield
With pyridine

cholest-5-en-3β,7β-diol (566-27-8) + benzoic acid anhydride (93-97-0) → 7-dehydrocholesterol (434-16-2)

Conditions	Yield
at 180 - 190℃;

cholest-5-en-3β,7β-diol (566-27-8) + benzoic acid anhydride (93-97-0) → 3β,7β-cholest-5-ene-3,7-diol-3-benzoate (17974-80-0)

Conditions	Yield
With benzene
With toluene
With xylene

Upstream product

• 809-51-8 7-ketocholesteryl acetate 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 604-35-3 Cholesteryl acetate 
• 36871-91-7 7β-hydroperoxy-3β-hydroxycholest-5-ene 
• 18099-24-6 cholest-5-ene-3β,7β-diol diacetate 
• 57-88-5 cholesterol 
• 7732-18-5 water 
• 60-29-7 diethyl ether 
• 57-88-5 cholesterol 
• 17974-77-5 3β-acetoxy-7β-hydroxycholest-5-ene 
• 57-88-5 Epicholesterol 
• 2846-29-9 7α-Hydroperoxycholest-5-en-3α-ol 
• 75-91-2 tert.-butylhydroperoxide 

Downstream Products

• 434-16-2 7-dehydrocholesterol 
• 17974-80-0 3β,7β-cholest-5-ene-3,7-diol-3-benzoate 
• 6038-38-6 3β,7β-bis-benzoyloxy-cholest-5-ene 
• 57-88-5 cholesterol 
• 80-97-7 Cholestanol 
• 566-25-6 5α-cholestane-3β,7β-diol 
• 5895-91-0 3β-(3,5-dinitro-benzoyloxy)-cholesta-5,7-diene 
• 1182-06-5 3β-benzoyloxycholesta-5,7-diene 
• 16826-37-2 5α-cholest-7-ene-3β-ol acetate 
• 6562-21-6 3β-(Acetyloxy)-5α-cholest-8(14)-ene 
• 15459-85-5 5α-cholest-7-en-3-one 
• 80-99-9 lathosterol 
• 21170-14-9 3β-acetoxycholest-5-en-7β-yl benzoate 
• 809-51-8 7-ketocholesteryl acetate 

Relevant articles and documents

Cholesterol degradation in archaeological pottery mediated by fired clay and fatty acid pro-oxidants

Cholesterol is generally absent in animal fat residues preserved in archaeological ceramic vessels. It is known from edible oil refining that during bleaching with activated clay sterols are degraded, largely via oxidation. Laboratory heating experiments

Metal-Free Allylic Oxidation of Steroids Using TBAI/TBHP Organocatalytic Protocol

A mild, efficient and organocatalytic allylic oxidation of steroids using a TBAI/TBHP protocol has been developed. A range of bioactive Δ5-en-7-ones can be easily prepared from the corresponding Δ5-steroids. The methodology features several advantages, including readily available starting materials, environmentally benign oxidant, high functional group compatibility, and metal-free catalysis.

Cholesterol transformations during heat treatment

The aim of the study was to characterise products of cholesterol standard changes during thermal processing. Cholesterol was heated at 120 °C, 150 °C, 180 °C and 220 °C from 30 to 180 min. The highest losses of cholesterol content were found during thermal processing at 220 °C, whereas the highest content of cholesterol oxidation products was observed at temperature of 150 °C. The production of volatile compounds was stimulated by the increase of temperature. Treatment of cholesterol at higher temperatures i.e. 180 °C and 220 °C led to the formation of polymers and other products e.g. cholestadienes and fragmented cholesterol molecules. Further studies are required to identify the structure of cholesterol oligomers and to establish volatile compounds, which are markers of cholesterol transformations, mainly oxidation.