Conditions | Yield |
---|---|
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 |
tirucallol
Conditions | Yield |
---|---|
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 | Yield |
---|---|
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
tirucallol
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol; benzene for 240h; Ambient temperature; | 19% |
Conditions | Yield |
---|---|
ueber mehrere Stufen; |
cycloartenol
A
parkeol
B
tirucallol
C
Cucurbita-5(10),24-dien-3β-ol
D
tirucalla-7,24-dien-3β-ol
Conditions | Yield |
---|---|
With sulfuric acid In isopropyl alcohol at 80℃; for 12h; Further byproducts given; |
3β-acetoxy-24ξ-hydroxylanost-8-ene
A
24,25-dihydrolanosterol
B
tirucallol
Conditions | Yield |
---|---|
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
tirucallol
Conditions | Yield |
---|---|
(i) SO3, Py, THF, (ii) LiAlH4; Multistep reaction; |
Conditions | Yield |
---|---|
With CAS1Ile841Val mutant; YPG+heme rearrangement; cyclization; |
cycloartenol
A
parkeol
B
tirucallol
C
Cucurbita-5(10),24-dien-3β-ol
D
10α-cucurbita-5,24-diene-3β-ol
E
tirucalla-7,24-dien-3β-ol
F
5α-Lanosta-9(11),25-dien-3β-ol
Conditions | Yield |
---|---|
With sulfuric acid In isopropyl alcohol at 80℃; for 12h; Product distribution; |
Conditions | Yield |
---|---|
With S. cerevisiae lanosterol synthase Val454Gly mutant at 20℃; pH=6.2; Product distribution; Further Variations:; Reagents; Cyclization; Enzymatic reaction; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With cycloartenol synthase AtCAS1 Tyr410Cys mutant Product distribution; Further Variations:; Reagents; |
2,3-oxidosqualene
tirucallol
Conditions | Yield |
---|---|
With baker's yeast Saccharomyces cerevisiae on calcium alginate In diethyl ether at 30℃; for 20h; pH=7.4; Enzymatic reaction; |
Conditions | Yield |
---|---|
With lanosterol synthase mutant SceErg7 Tyr510His In water at 20℃; for 24h; pH=6.2; Product distribution; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
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
tirucallol
Conditions | Yield |
---|---|
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 |
tirucallol
Conditions | Yield |
---|---|
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
tirucallol
Conditions | Yield |
---|---|
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
tirucallol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaBH4 / aq. ethanol 2: (i) SO3, Py, THF, (ii) LiAlH4 View Scheme |
squalene 2,3(S)-oxide
A
(9R,10S)-polypoda-8(26),13E,17E,21-tetraen-3β-ol
B
parkeol
C
tirucallol
Conditions | Yield |
---|---|
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707Q Enzymatic reaction; |
squalene 2,3(S)-oxide
A
(9R,10S)-polypoda-8(26),13E,17E,21-tetraen-3β-ol
B
parkeol
C
tirucallol
Conditions | Yield |
---|---|
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707H Enzymatic reaction; |
Conditions | Yield |
---|---|
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707F Enzymatic reaction; |
squalene 2,3(S)-oxide
tirucallol
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclaseY707I Enzymatic reaction; |
squalene 2,3(S)-oxide
A
(13αH)-isomalabarica-14Z,17E,21-trien-3β-ol
B
(13αH)-isomalabarica-14E,17E,21-trien-3β-ol
C
tirucallol
Conditions | Yield |
---|---|
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
A
(13αH)-isomalabarica-14Z,17E,21-trien-3β-ol
B
tirucallol
Conditions | Yield |
---|---|
With Saccharomyces cerevisiae TKW14 expressing ERG7(Y99E) mutant Microbiological reaction; |
squalene 2,3(S)-oxide
C
tirucallol
Conditions | Yield |
---|---|
With Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase ERG7(Phe699His) mutant |
Conditions | Yield |
---|---|
With Aspergillus fumigatus oxidosqualene:protostadienol cyclase 702NKSCAIS708 mutant at 30℃; for 1h; Kinetics; Enzymatic reaction; |
lanosta-8,24-dien-3-one
A
tirucallol
B
lanosta-8,24-dien-3α-ol
Conditions | Yield |
---|---|
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 |
tirucallol
24,25-dihydrolanosterol
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at 0℃; for 0.333333h; | 100% |
3,4-dihydro-2H-pyran
tirucallol
3β-Tetrahydropyranyl lanosterol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane | 100% |
With pyridinium p-toluenesulfonate In dichloromethane for 5h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
With pyridine at 20℃; for 12h; | 84% |
With pyridine at 20℃; for 12h; | 84% |
tirucallol
2,8,24-lanostatriene
Conditions | Yield |
---|---|
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
N,N-dimethyl-formamide
lanosta-8,24-dien-3β-yl formate
Conditions | Yield |
---|---|
With diphenylphosphinopolystyrene; iodine In dichloromethane at 50℃; for 2h; | 92% |
With trichlorophosphate at 5 - 20℃; for 4h; | 91% |
Conditions | Yield |
---|---|
With pyridine at 0℃; for 72h; | 91% |
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
Conditions | Yield |
---|---|
With sodium hydride; methyl iodide In tetrahydrofuran at 20℃; for 12h; | 90% |
tirucallol
4,5-dichloroisothiazole-3-carboxylic acid chloride
Conditions | Yield |
---|---|
With pyridine In diethyl ether at 20 - 23℃; | 88% |
2-bromo-3,4,4-trichloro-3-butenoyl chloride
tirucallol
Conditions | Yield |
---|---|
With pyridine In benzene at 20 - 23℃; | 87% |
Conditions | Yield |
---|---|
With pyridine In benzene Heating; | 86% |
tirucallol
3,3,4-trichloro-3-butenoyl chloride
Conditions | Yield |
---|---|
With pyridine In diethyl ether at 20 - 23℃; | 82% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
tirucallol
4-[(3β)-lanosta-8,24-dien-3-yloxy]-4-oxobutanoic acid
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 168h; | 79% |
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
Conditions | Yield |
---|---|
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
tirucallol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane for 2h; | 73% |
tirucallol
lanosta-8,24-dien-3-one
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
DBN In tetrahydrofuran at 50 - 70℃; for 3h; Formylation; | 70% |
tirucallol
(3S,5R,10S,13R,14R,17R,20R)-24,25-epoxylanosterol
Conditions | Yield |
---|---|
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
24-methylenelanost-8-en-3-ol
Conditions | Yield |
---|---|
With Paracoccidiodes brasiliensis sterol C24-methyltransferase, recombinant; AdoMet Enzymatic reaction; | 55% |
tirucallol
lanosteryl phosphorodichloridate
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate In acetone at 0℃; for 4h; | 49% |
With pyridine; trichlorophosphate In acetone |
tirucallol
Conditions | Yield |
---|---|
With oxygen; rose bengal In methanol for 2h; UV-irradiation; | 5% |
tirucallol
Conditions | Yield |
---|---|
With diethylamino-sulfur trifluoride In n-heptane; dichloromethane at 20℃; for 0.166667h; Inert atmosphere; | 1% |
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
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View