Product Name

  • Name

    LANOSTEROL

  • EINECS 201-214-9
  • CAS No. 79-63-0
  • Article Data25
  • CAS DataBase
  • Density 0.988 g/cm3
  • Solubility
  • Melting Point 137 °C
  • Formula C30H50O
  • Boiling Point 498.855 °C at 760 mmHg
  • Molecular Weight 426.726
  • Flash Point 221.143 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 79-63-0 (LANOSTEROL)
  • Hazard Symbols
  • Synonyms Lanosta-8,24-dien-3b-ol (8CI);Lanostadien-3b-ol (7CI);Lanosterol (6CI);3b-Hydroxylanosta-8,24-diene;4,4,14a-Trimethylcholesta-8,24-dien-3b-ol;5a-Lanosta-8,24-dien-3b-ol;Lanosta-8,24-dienol;Lanosterin;Lanster;NSC60677;
  • PSA 20.23000
  • LogP 8.47910

Synthetic route

O-acetyl-lanosterol
2671-68-3

O-acetyl-lanosterol

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 72h; Ambient temperature;94%
With potassium hydroxide In ethanol at 60℃; for 2h;
Multi-step reaction with 3 steps
1: SeO2 / aq. ethanol
2: NaBH4 / aq. ethanol
3: (i) SO3, Py, THF, (ii) LiAlH4
View Scheme
Conditions
ConditionsYield
With Trypanosoma cruzi LHY4-[pBJ1.22] transformant at 25℃; for 24h;82%
With K-phosphate buffer; Triton X-100 In water at 37℃; for 5h; oxidosqualene-lanosterol cyclase; effect of various detergents;
With Trypanosoma cruzi oxidosqualene cyclase; 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt In dimethylsulfoxide-d6; aq. phosphate buffer at 37℃; pH=7; Reagent/catalyst; Enzymatic reaction;
Conditions
ConditionsYield
With S. cerevisiae lanosterol-synthase Thr 384 Tyr mutant Product distribution; Further Variations:; Reagents;A 11%
B 79%
C 10%
Octanoic acid (3S,5R,10S,13R,14R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
124770-75-8

Octanoic acid (3S,5R,10S,13R,14R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol; benzene for 240h; Ambient temperature;19%
cholesterol
57-88-5

cholesterol

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
ueber mehrere Stufen;
cycloartenol
469-38-5

cycloartenol

A

parkeol
514-45-4

parkeol

B

tirucallol
79-63-0

tirucallol

C

Cucurbita-5(10),24-dien-3β-ol
110654-88-1

Cucurbita-5(10),24-dien-3β-ol

D

tirucalla-7,24-dien-3β-ol
23515-91-5

tirucalla-7,24-dien-3β-ol

Conditions
ConditionsYield
With sulfuric acid In isopropyl alcohol at 80℃; for 12h; Further byproducts given;
3β-acetoxy-24ξ-hydroxylanost-8-ene
20905-52-6

3β-acetoxy-24ξ-hydroxylanost-8-ene

B

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; trichlorophosphate 1.) pyridine, 5 h, reflux, 2.) dioxane, 10 h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
3β-acetoxy-(24E)-lanostadiene-8,24 ol-26
68612-46-4

3β-acetoxy-(24E)-lanostadiene-8,24 ol-26

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
(i) SO3, Py, THF, (ii) LiAlH4; Multistep reaction;
Conditions
ConditionsYield
With CAS1Ile841Val mutant; YPG+heme rearrangement; cyclization;
cycloartenol
469-38-5

cycloartenol

A

parkeol
514-45-4

parkeol

B

tirucallol
79-63-0

tirucallol

C

Cucurbita-5(10),24-dien-3β-ol
110654-88-1

Cucurbita-5(10),24-dien-3β-ol

D

10α-cucurbita-5,24-diene-3β-ol
35012-08-9

10α-cucurbita-5,24-diene-3β-ol

E

tirucalla-7,24-dien-3β-ol
23515-91-5

tirucalla-7,24-dien-3β-ol

F

5α-Lanosta-9(11),25-dien-3β-ol
129763-89-9

5α-Lanosta-9(11),25-dien-3β-ol

G

other alcohols, and dehydration products

other alcohols, and dehydration products

Conditions
ConditionsYield
With sulfuric acid In isopropyl alcohol at 80℃; for 12h; Product distribution;
Conditions
ConditionsYield
With S. cerevisiae lanosterol synthase Val454Gly mutant at 20℃; pH=6.2; Product distribution; Further Variations:; Reagents; Cyclization; Enzymatic reaction;
Conditions
ConditionsYield
With Arabidopsis thaliana cycloartenol synthase Ile481Gly; Triton X-100 In phosphate buffer for 24h; pH=6.4; Product distribution; Further Variations:; Reagents; Cyclization; Enzymatic reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

tirucallol
79-63-0

tirucallol

B

(-)-achilleol A
125287-06-1

(-)-achilleol A

C

9β-lanosta-7,24-dien-3β-ol

9β-lanosta-7,24-dien-3β-ol

Conditions
ConditionsYield
With cycloartenol synthase AtCAS1 Tyr410Cys mutant Product distribution; Further Variations:; Reagents;
2,3-oxidosqualene
147731-51-9

2,3-oxidosqualene

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With baker's yeast Saccharomyces cerevisiae on calcium alginate In diethyl ether at 30℃; for 20h; pH=7.4; Enzymatic reaction;

A

(13αH)-isomalabarica-14(26),17E,21-trien-3β-ol

(13αH)-isomalabarica-14(26),17E,21-trien-3β-ol

B

parkeol
514-45-4

parkeol

C

tirucallol
79-63-0

tirucallol

D

(-)-achilleol A
125287-06-1

(-)-achilleol A

Conditions
ConditionsYield
With lanosterol synthase mutant SceErg7 Tyr510His In water at 20℃; for 24h; pH=6.2; Product distribution; Further Variations:; Reagents;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

parkeol
514-45-4

parkeol

B

cycloartenol
469-38-5

cycloartenol

C

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With cycloartenol synthase I481V mutant In phosphate buffer at 20℃; for 24h; pH=7.4; Product distribution; Further Variations:; Reagents;
24(R,S)-3β-acetoxy-24,25-dihydroxy-5α-lanost-8-ene
63976-67-0, 63976-68-1, 20905-61-7

24(R,S)-3β-acetoxy-24,25-dihydroxy-5α-lanost-8-ene

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CH2Cl2 / 2.5 h / Heating
2: 8.3 g / Ac2O / 3.5 h / 130 °C
3: KOH / ethanol / 2 h / 60 °C
View Scheme
Acetic acid (3S,5R,10S,13R,14R,17R)-17-[(R)-3-(2-dimethylamino-5,5-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-propyl]-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Acetic acid (3S,5R,10S,13R,14R,17R)-17-[(R)-3-(2-dimethylamino-5,5-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-propyl]-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 8.3 g / Ac2O / 3.5 h / 130 °C
2: KOH / ethanol / 2 h / 60 °C
View Scheme
3β-acetoxy-lanost-8-en-24-one
13553-26-9

3β-acetoxy-lanost-8-en-24-one

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.25 g / NaBH4 / tetrahydrofuran / 96 h / Ambient temperature
2: 1.) POCl3, 2.) LiAlH4 / 1.) pyridine, 5 h, reflux, 2.) dioxane, 10 h, reflux
View Scheme
3β-acetoxy-(24E)-lanosta-8,24-dien-26-al
68612-49-7

3β-acetoxy-(24E)-lanosta-8,24-dien-26-al

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4 / aq. ethanol
2: (i) SO3, Py, THF, (ii) LiAlH4
View Scheme
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

(9R,10S)-polypoda-8(26),13E,17E,21-tetraen-3β-ol
1073543-01-7

(9R,10S)-polypoda-8(26),13E,17E,21-tetraen-3β-ol

B

parkeol
514-45-4

parkeol

C

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707Q Enzymatic reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

(9R,10S)-polypoda-8(26),13E,17E,21-tetraen-3β-ol
1073543-01-7

(9R,10S)-polypoda-8(26),13E,17E,21-tetraen-3β-ol

B

parkeol
514-45-4

parkeol

C

tirucallol
79-63-0

tirucallol

D

9β-lanosta-7,24-dien-3β-ol

9β-lanosta-7,24-dien-3β-ol

Conditions
ConditionsYield
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707H Enzymatic reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

parkeol
514-45-4

parkeol

B

tirucallol
79-63-0

tirucallol

C

9β-lanosta-7,24-dien-3β-ol

9β-lanosta-7,24-dien-3β-ol

Conditions
ConditionsYield
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707F Enzymatic reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707V Enzymatic reaction;
With Saccharomyces cerevisiae TKW14 expressing ERG7(Y99V) mutant Microbiological reaction;
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase ERG7(Phe699Leu) mutant
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase ERG7C7O3D Reagent/catalyst; Enzymatic reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

tirucallol
79-63-0

tirucallol

B

9β-lanosta-7,24-dien-3β-ol

9β-lanosta-7,24-dien-3β-ol

Conditions
ConditionsYield
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707I Enzymatic reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

(13αH)-isomalabarica-14Z,17E,21-trien-3β-ol
1203607-72-0

(13αH)-isomalabarica-14Z,17E,21-trien-3β-ol

B

(13αH)-isomalabarica-14E,17E,21-trien-3β-ol
1203607-73-1

(13αH)-isomalabarica-14E,17E,21-trien-3β-ol

C

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With Saccharomyces cerevisiae TKW14 expressing ERG7(Y99A) mutant Microbiological reaction;
With Saccharomyces cerevisiae TKW14 expressing ERG7(Y99I) mutant Microbiological reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

(13αH)-isomalabarica-14Z,17E,21-trien-3β-ol
1203607-72-0

(13αH)-isomalabarica-14Z,17E,21-trien-3β-ol

B

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With Saccharomyces cerevisiae TKW14 expressing ERG7(Y99E) mutant Microbiological reaction;
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

protosta-13(17)-dien-3β-ol

protosta-13(17)-dien-3β-ol

B

(17Z)-protosta-17(20),24-dien-3β-ol

(17Z)-protosta-17(20),24-dien-3β-ol

C

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase ERG7(Phe699His) mutant
squalene 2,3(S)-oxide
54910-48-4

squalene 2,3(S)-oxide

A

parkeol
514-45-4

parkeol

B

tirucallol
79-63-0

tirucallol

Conditions
ConditionsYield
With Aspergillus fumigatus oxidosqualene:protostadienol cyclase 702NKSCAIS708 mutant at 30℃; for 1h; Kinetics; Enzymatic reaction;
lanosta-8,24-dien-3-one
13879-13-5, 54325-09-6, 5539-04-8

lanosta-8,24-dien-3-one

A

tirucallol
79-63-0

tirucallol

B

lanosta-8,24-dien-3α-ol
76582-59-7

lanosta-8,24-dien-3α-ol

Conditions
ConditionsYield
With potassium hydroxide In ethylene glycol for 5h; Reflux; optical yield given as %de;
With C36H103AlO4Si14; isopropyl alcohol In neat (no solvent) at 70℃; for 24h; Meerwein-Ponndorf-Verley Reduction; Glovebox; Schlenk technique;A n/a
B n/a
Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In dichloromethane at 20℃; under 2585.81 Torr; for 24h;100%
With ammonium formate; palladium on activated charcoal In dichloromethane for 7h; Irradiation;80%
With hydrogen; platinum(IV) oxide
With hydrogen; palladium on activated charcoal In ethyl acetate; toluene at 20℃; for 17h;
With palladium on activated charcoal; hydrogen In ethyl acetate; phenol at 20℃;
tirucallol
79-63-0

tirucallol

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

Lanosterin-trifluoracetat
10112-12-6

Lanosterin-trifluoracetat

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0℃; for 0.333333h;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

tirucallol
79-63-0

tirucallol

3β-Tetrahydropyranyl lanosterol
84882-57-5, 144407-65-8

3β-Tetrahydropyranyl lanosterol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane100%
With pyridinium p-toluenesulfonate In dichloromethane for 5h; Ambient temperature; Yield given;
tirucallol
79-63-0

tirucallol

acetic anhydride
108-24-7

acetic anhydride

O-acetyl-lanosterol
2671-68-3

O-acetyl-lanosterol

Conditions
ConditionsYield
With pyridine at 20℃;100%
With pyridine at 20℃; for 12h;84%
With pyridine at 20℃; for 12h;84%
tirucallol
79-63-0

tirucallol

2,8,24-lanostatriene
106065-41-2

2,8,24-lanostatriene

Conditions
ConditionsYield
With sodium tosylate; thiamine diphosphate; diethylazodicarboxylate In tetrahydrofuran for 1.25h; Heating;95%
With 5%-palladium/activated carbon; hydrogen In ethyl acetate; benzene at 20℃; Inert atmosphere;
tirucallol
79-63-0

tirucallol

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

lanosta-8,24-dien-3β-yl formate
115045-75-5

lanosta-8,24-dien-3β-yl formate

Conditions
ConditionsYield
With diphenylphosphinopolystyrene; iodine In dichloromethane at 50℃; for 2h;92%
With trichlorophosphate at 5 - 20℃; for 4h;91%
tirucallol
79-63-0

tirucallol

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

lanost-8-en-3β-yl benzenesulfonate

lanost-8-en-3β-yl benzenesulfonate

Conditions
ConditionsYield
With pyridine at 0℃; for 72h;91%
tirucallol
79-63-0

tirucallol

(3S,5R,10S,13R,14R,17R)-3-methoxy-4,4,10,13,14-pentamethyl-17-((R)-6-methylhept-5-en-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
88165-78-0, 107242-94-4

(3S,5R,10S,13R,14R,17R)-3-methoxy-4,4,10,13,14-pentamethyl-17-((R)-6-methylhept-5-en-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

Conditions
ConditionsYield
With sodium hydride; methyl iodide In tetrahydrofuran at 20℃; for 12h;90%
tirucallol
79-63-0

tirucallol

4,5-dichloroisothiazole-3-carboxylic acid chloride
220769-88-0

4,5-dichloroisothiazole-3-carboxylic acid chloride

4,5-Dichloro-isothiazole-3-carboxylic acid (3S,5R,10S,13R,14R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

4,5-Dichloro-isothiazole-3-carboxylic acid (3S,5R,10S,13R,14R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions
ConditionsYield
With pyridine In diethyl ether at 20 - 23℃;88%
2-bromo-3,4,4-trichloro-3-butenoyl chloride
913966-90-2

2-bromo-3,4,4-trichloro-3-butenoyl chloride

tirucallol
79-63-0

tirucallol

lanosterolyl 2-bromo-3,4,4-trichlorobut-3-enoate

lanosterolyl 2-bromo-3,4,4-trichlorobut-3-enoate

Conditions
ConditionsYield
With pyridine In benzene at 20 - 23℃;87%
tirucallol
79-63-0

tirucallol

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

lanosteryl 1-adamantylmethanoate

lanosteryl 1-adamantylmethanoate

Conditions
ConditionsYield
With pyridine In benzene Heating;86%
tirucallol
79-63-0

tirucallol

3,3,4-trichloro-3-butenoyl chloride
484067-66-5

3,3,4-trichloro-3-butenoyl chloride

3β-lanosteryl 3,4,4-trichloro-3-butenoate

3β-lanosteryl 3,4,4-trichloro-3-butenoate

Conditions
ConditionsYield
With pyridine In diethyl ether at 20 - 23℃;82%
tirucallol
79-63-0

tirucallol

(R)-1,2-dithiolane-3-pentanoic acid
1200-22-2

(R)-1,2-dithiolane-3-pentanoic acid

C38H62O2S2

C38H62O2S2

Conditions
ConditionsYield
Stage #1: (R)-1,2-dithiolane-3-pentanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 5℃; for 0.0833333h;
Stage #2: With triethylamine In dichloromethane at 0 - 5℃; for 0.916667h;
Stage #3: tirucallol With dmap In dichloromethane at 25 - 30℃; for 5h; Enzymatic reaction;
82%
isopropyldimethylsilyl chloride
3634-56-8

isopropyldimethylsilyl chloride

tirucallol
79-63-0

tirucallol

C35H62OSi

C35H62OSi

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 10h;80%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 10h;80%
succinic acid anhydride
108-30-5

succinic acid anhydride

tirucallol
79-63-0

tirucallol

4-[(3β)-lanosta-8,24-dien-3-yloxy]-4-oxobutanoic acid
1014978-53-0

4-[(3β)-lanosta-8,24-dien-3-yloxy]-4-oxobutanoic acid

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 168h;79%
tirucallol
79-63-0

tirucallol

(4R)-4-((5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanal
1345457-17-1

(4R)-4-((5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanal

Conditions
ConditionsYield
Stage #1: tirucallol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60 - -20℃; for 0.0333333h; Swern oxidation; Inert atmosphere;
Stage #2: With triethylamine In dichloromethane at -20 - 25℃; Swern oxidation; Inert atmosphere;
Stage #3: With ozone In dichloromethane at -50℃; for 0.283333h; Inert atmosphere;
78%
(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid
2596-47-6, 147677-05-2, 34749-55-8

(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid

tirucallol
79-63-0

tirucallol

3-O-(trans-4-O-acetylferuloyl)-8,24,(5-α)-cholestandien-4,4,14-α-trimethyl-3-β-ol

3-O-(trans-4-O-acetylferuloyl)-8,24,(5-α)-cholestandien-4,4,14-α-trimethyl-3-β-ol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;77%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

tirucallol
79-63-0

tirucallol

Isonicotinic acid (3S,5R,10S,13R,14R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Isonicotinic acid (3S,5R,10S,13R,14R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane for 2h;73%
tirucallol
79-63-0

tirucallol

lanosta-8,24-dien-3-one
13879-13-5, 54325-09-6, 5539-04-8

lanosta-8,24-dien-3-one

Conditions
ConditionsYield
With quinolinium chlorochromate(VI) In dichloromethane at 20℃; for 18h;70%
With chromium trioxide pyridine In dichloromethane for 24h; Ambient temperature;65%
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;45%
β-oxopropyl formate
10258-70-5

β-oxopropyl formate

tirucallol
79-63-0

tirucallol

lanosta-8,24-dien-3β-yl formate
115045-75-5

lanosta-8,24-dien-3β-yl formate

Conditions
ConditionsYield
DBN In tetrahydrofuran at 50 - 70℃; for 3h; Formylation;70%
tirucallol
79-63-0

tirucallol

(3S,5R,10S,13R,14R,17R,20R)-24,25-epoxylanosterol
18303-41-8

(3S,5R,10S,13R,14R,17R,20R)-24,25-epoxylanosterol

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 3h;70%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Cooling with ice;
tirucallol
79-63-0

tirucallol

24-methylenelanost-8-en-3-ol
516-28-9, 566-14-3, 97719-41-0, 6890-88-6

24-methylenelanost-8-en-3-ol

Conditions
ConditionsYield
With Paracoccidiodes brasiliensis sterol C24-methyltransferase, recombinant; AdoMet Enzymatic reaction;55%
tirucallol
79-63-0

tirucallol

lanosteryl phosphorodichloridate
24352-48-5

lanosteryl phosphorodichloridate

Conditions
ConditionsYield
With pyridine; trichlorophosphate In acetone at 0℃; for 4h;49%
With pyridine; trichlorophosphate In acetone
tirucallol
79-63-0

tirucallol

inoterpene C

inoterpene C

Conditions
ConditionsYield
With oxygen; rose bengal In methanol for 2h; UV-irradiation;5%
tirucallol
79-63-0

tirucallol

3α-fluorolanosterol

3α-fluorolanosterol

Conditions
ConditionsYield
With diethylamino-sulfur trifluoride In n-heptane; dichloromethane at 20℃; for 0.166667h; Inert atmosphere;1%

Lanosta-8,24-dien-3-ol,(3beta)- Specification

The Lanosta-8,24-dien-3-ol,(3beta)- is an organic compound with the formula C30H50O. The IUPAC name of this chemical is (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol. With the CAS registry number 79-63-0, it is also named as (3β)-Lanosta-8,24-dien-3-ol. The product's categories are Miscellaneous Natural Products; Organics; Biochemistry; Hydroxysteroids; Steroids. Besides, it should be stored in a closed and cool place. It is used for atherosclerosis research.

Physical properties about Lanosta-8,24-dien-3-ol,(3beta)- are: (1)ACD/LogP: 10.52; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 10.521; (4)ACD/LogD (pH 7.4): 10.521; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.53; (14)Molar Refractivity: 133.401 cm3; (15)Molar Volume: 431.845 cm3; (16)Polarizability: 52.884×10-24cm3; (17)Surface Tension: 37.965 dyne/cm; (18)Density: 0.988 g/cm3; (19)Flash Point: 221.143 °C; (20)Enthalpy of Vaporization: 88.348 kJ/mol; (21)Boiling Point: 498.855 °C at 760 mmHg.

Uses of Lanosta-8,24-dien-3-ol,(3beta)-: it can be used to produce (5a)-euph-8-en-3b-ol at ambient temperature. It will need reagent H2, catalyst Pd/C (10 percent) and solvent ethanol with reaction time of 4 hours. The yield is about 85%.

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
(2)InChI:InChI=1/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
(3)InChIKey: CAHGCLMLTWQZNJ-BQNIITSRBP
(4)Std. InChI: InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
(5)Std. InChIKey: CAHGCLMLTWQZNJ-BQNIITSRSA-N

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