Betulin supplier | CasNO.473-98-3

Name
Betulin
EINECS 207-475-5
CAS No. 473-98-3
Article Data34
CAS DataBase
Density 1.017 g/cm³
Solubility
Melting Point 256-257 °C(lit.)
Formula C₃₀H₅₀O₂
Boiling Point 522.275 °C at 760mm Hg
Molecular Weight 442.726
Flash Point 210.873 °C
Transport Information
Appearance white crystalline powder
Safety 36/37-36-26
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Lup-20(29)-ene-3b,28-diol(8CI);Lup-20(30)-ene-3b,28-diol (6CI);3aH-Cyclopenta[a]chrysene,lup-20(29)-ene-3,28-diol deriv.;(+)-Betulin;3,28-Dihydroxy-lupeol;3b,28-Dihydroxylup-20(29)-ene;Betuline;Betulinic alcohol;Betulinol;Betulol;NSC 4644;Trochol;Birch bark Extract;
PSA 40.46000
LogP 6.99720

Synthetic route

: 1721-69-3
betulin diacetate

: 473-98-3
betulin

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 2h; Heating;	96%
With potassium hydroxide; ethanol In toluene for 2h; Heating / reflux;	93%
With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 168000h;

: 3,28-bis(O-THP)-betulin

: 473-98-3
betulin

Conditions

Conditions	Yield
With montmorillonite K-10 In methanol at 40 - 50℃; for 2h;	95%

: betulin 3,28-bis-O-trifluoroacetate

: 473-98-3
betulin

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; toluene at 60℃; for 3h;	94%

: 472-15-1
Betulinic acid

A: 473-98-3
betulin

B: 13159-28-9, 92594-07-5
betulinic aldehyde

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;	A 90% B 5%

: 472-15-1
Betulinic acid

: 473-98-3
betulin

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Reflux; Inert atmosphere; Sealed tube;	90%
Multi-step reaction with 2 steps 1: 1 g / diethyl ether; CH2Cl2 / 0 °C 2: 0.65 g / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 2: LAH View Scheme

: 1721-69-3
betulin diacetate

A: 473-98-3
betulin

B: 27570-20-3
betulin monoacetate

Conditions

Conditions	Yield
With calcium hydroxide In methanol; chloroform for 24h; Ambient temperature;	A 10% B 89%
With magnesium methanolate In tetrahydrofuran; methanol for 72h; Ambient temperature;	A 14% B 81%
With sodium methylate In tetrahydrofuran; methanol for 48h; Ambient temperature;	A 53.1% B 43.4%

: 2259-06-5, 25493-95-2
methyl betulinate

: 473-98-3
betulin

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 10 - 20℃;	76%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 3h; Heating;
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;	0.65 g

: 13159-28-9, 92594-07-5
betulinic aldehyde

: 292638-85-8
acrylic acid methyl ester

A: 1228273-12-8
(R)-4-[3β-hydroxy-28-norlup-20(29)-en-17β-yl]-γ-butyrolactone

B: 473-98-3
betulin

Conditions

Conditions	Yield
With samarium; 1,2-Diiodoethane; tert-butyl alcohol In tetrahydrofuran at 0℃; Inert atmosphere;	A 47% B n/a

...Expand

: 4439-98-9
betulonic aldehyde

A: 473-98-3
betulin

B: 3-epi-betulinic aldehyde

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; L-Selectride 1.) THF, -20 deg C, min, 2.) THF, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

betulinic acid: betulinic acid

: 473-98-3
betulin

Conditions

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether

: 67-56-1
methanol

: betulin 3-O-palmitate

A: 112-39-0
hexadecanoic acid methyl ester

B: 473-98-3
betulin

Conditions

Conditions	Yield
With potassium hydroxide for 3h; Heating;

...Expand

: 1256450-16-4
3β-O-cis-feruloylbetulin

: 473-98-3
betulin

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 65℃; for 10h;

: 27686-35-7
28-acetoxybetulin

: 107-13-1
acrylonitrile

A: 1239919-26-6
3-[3β-hydroxylup-20(29)-en-28-yloxy]propanenitrile

B: 473-98-3
betulin

C: 1309960-59-5
3β-(2-cyanoethoxy)lup-20(29)-en-28-yl acetate

D: 1309960-47-1
3β,28-di(2-cyanoethoxy)lup-20(29)-ene

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In 1,4-dioxane; water at 20℃; for 24h; Inert atmosphere;	A 5 %Chromat. B 22 %Chromat. C 64 %Chromat. D 9 %Chromat.

...Expand

: 3-O-myristoylbetulin

: 473-98-3
betulin

Conditions

Conditions	Yield
With methanol; potassium hydroxide for 2h;

: 3β-O-cis-caffeoylbetulin

: 473-98-3
betulin

Conditions

Conditions	Yield
With potassium hydroxide at 20℃; for 12h;

: 473-98-3
betulin

: 55029-05-5, 7372-31-8
lupane-3β,28-diol

Conditions

Conditions	Yield
With hydrogen; 10percent Pd/C In tetrahydrofuran; methanol under 2068.65 Torr;	100%
With hydrogen; palladium 10% on activated carbon In methanol; dichloromethane under 1810.07 Torr; for 16h;	100%
With hydrogen; platinum(IV) oxide In methanol; chloroform for 8h;	99%

: 473-98-3
betulin

: 108-24-7
acetic anhydride

: 1721-69-3
betulin diacetate

Conditions

Conditions	Yield
With pyridine; dmap at 20℃; for 1h;	100%
With dmap In tetrahydrofuran at 20℃;	100%
montmorillonite acid clay for 0.0333333h; microwave irradiation;	99%

: 473-98-3
betulin

: 1617-72-7, 5713-24-6, 125225-35-6, 137173-47-8
allobetulin

Conditions

Conditions	Yield
Montmorillonite KSF In dichloromethane for 3.5h; Heating;	99%
With trifluoroacetic acid In chloroform at 22℃; for 0.133333h;	97%
With amberlyst 15 In chloroform Reflux;	96%

: 473-98-3
betulin

: 6714-21-2
19β,28-epoxy-A-neo-18α-olean-3(5)-ene

Conditions

Conditions	Yield
With bithmuth(III) triflate hydrate In dichloromethane for 40h; Reflux;	98%
With kieselguhr; xylene
Multi-step reaction with 2 steps 1: 99 percent / montmorillonite KSF / CH2Cl2 / 3.5 h / Heating 2: 65 percent / montmorillonite K10 / cyclohexane / 2.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 68 percent / PCl5 / petroleum ether / 1.) 0 deg C, 30 min, 2.) r.t., 45 min 2: 61 percent / montmorillonite K10 / CH2Cl2 / 40 °C View Scheme

: 473-98-3
betulin

: 76-83-5
trityl chloride

: 431879-42-4
(3β)-28-(triphenylmethoxy)lup-20(29)-en-3-ol

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 60℃;	98%
With pyridine; dmap at 80℃;	85%
With pyridine; dmap In N,N-dimethyl-formamide Reflux; regioselective reaction;	76%

: 473-98-3
betulin

: 10543-60-9
2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo<3,3,0>octan-3,7-dione

: 1721-69-3
betulin diacetate

Conditions

Conditions	Yield
With trifluoroacetic acid In chloroform at 70℃; for 1h;	98%

: 473-98-3
betulin

A: 4439-98-9
betulonic aldehyde

B: 13159-28-9, 92594-07-5
betulinic aldehyde

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; 1,5-dimethyl-9-azanoradamantane N-oxyl In dichloromethane at 25℃; for 0.75h; Reagent/catalyst; Inert atmosphere;	A 51% B 97%
With pyridinium chlorochromate In dichloromethane at 20℃; for 1.5h;	A 82% B 17%
With 1‐methyl‐2‐azaadamantane‐N‐oxyl; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 2h; Catalytic behavior; Reagent/catalyst;	A 51% B 49%

: 473-98-3
betulin

: 13159-28-9, 92594-07-5
betulinic aldehyde

Conditions

Conditions	Yield
With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate In tetrahydrofuran; water at 20℃;	97%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; tetrabutylammomium bromide; sodium hypochlorite In phosphate buffer; dichloromethane at 35℃;	92%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; sodium hypochlorite In phosphate buffer; dichloromethane at 30℃; pH=6.8;	87%

: 75-77-4
chloro-trimethyl-silane

: 473-98-3
betulin

: 212708-99-1
O,O'-bis-(trimethylsilyl)-betulin

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; for 3h;	97%
With 1H-imidazole In dichloromethane at 25℃; for 3h;
With 1H-imidazole In dichloromethane at 0℃;

: 108-31-6
maleic anhydride

: 473-98-3
betulin

: (2Z,2′Z)-4,4′-[lup-20(29)-en-3β,28-diyl]bis(oxy)bis(4-oxobut-2-enoic acid)

Conditions

Conditions	Yield
With N,N-dimethyl-aniline In benzene for 50h; Reflux;	97%

: 85-44-9
phthalic anhydride

: 473-98-3
betulin

: 2519-35-9
betulin 3,28-bishemiphthalate

Conditions

Conditions	Yield
With pyridine for 15h; Addition; Heating;	96%
With pyridine; dmap for 30h; Heating;	76%
Stage #1: phthalic anhydride; betulin With pyridine; dmap for 37h; Heating / reflux; Stage #2: With hydrogenchloride In water; ethyl acetate	76%
With dmap for 24h;

: 473-98-3
betulin

: 19β,28-epoxy-A-neo-5β-methyl-25-nor-18α-olean-9(10)-ene

Conditions

Conditions	Yield
With bithmuth(III) triflate hydrate In dichloromethane for 8h; Reflux;	96%

: 110-87-2
3,4-dihydro-2H-pyran

: 473-98-3
betulin

: 189571-52-6
3-hydroxy-28-[(tetrahydro-2H-pyran-2-yl)oxy]lup-20(29)-ene

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane for 72h; Ambient temperature;	95%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 20h;	80%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 72h; Inert atmosphere;	57%

: 2623-87-2
bromobutyric acid

: 473-98-3
betulin

: 3β-hydroxylup-20(29)-en-28-yl 4-bromobutanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification;	95%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	80%

: 473-98-3
betulin

: 74-86-2
acetylene

: C32H52O2

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 80℃; for 2.5h;	95%

: 59-67-6
nicotinic acid

: 473-98-3
betulin

: 473806-27-8
3β,28-di-O-nicotinoyl-lupa-20(29)-ene

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 24h; regioselective reaction;	95%

: 6970-57-6
3-ethyl-3-methylglutaric anhydride

: 473-98-3
betulin

: 3-Ethyl-3-methyl-pentanedioic acid mono-[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxymethyl-3-methyl-pentanoyloxy)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-3a-ylmethyl] ester

Conditions

Conditions	Yield
With dmap In pyridine at 95℃;	94%
With pyridine; dmap at 95℃;

: 473-98-3
betulin

: betulin diphosphate

Conditions

Conditions	Yield
Stage #1: betulin With pyridine; trichlorophosphate In 1,4-dioxane at 10 - 20℃; for 24h; Stage #2: With water In 1,4-dioxane	94%
With pyridine; trichlorophosphate In acetone at 0℃; for 1h;	69%

: 473-98-3
betulin

: 1429785-14-7
30-iodolup-20(29)-ene-3β,28-diol

Conditions

Conditions	Yield
With iodine In N,N-dimethyl acetamide at 25℃; for 0.0166667h; Kinetics; Thermodynamic data; Concentration; Temperature; Solvent;	94%

: 473-98-3
betulin

: 20260-53-1
pyridine-3-carbonyl chloride hydrochloride

: betulin dinicotinate

Conditions

Conditions	Yield
With pyridine; tributyl-amine at 0 - 20℃; for 4h;	93.6%

: 473-98-3
betulin

: 4439-98-9
betulonic aldehyde

Conditions

Conditions	Yield
With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -30℃; Svern oxidation;	93%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -15 - 20℃; Swern oxidation;	93%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane Swern oxidation;	90%

: 473-98-3
betulin

: 98-89-5
Cyclohexanecarboxylic acid

A: Cyclohexanecarboxylic acid (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-3a-ylmethyl ester

B: Cyclohexanecarboxylic acid (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-hydroxymethyl-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl ester

C: C44H70O4

Conditions

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In chlorobenzene for 16h; Heating;	A 93% B n/a C 7%

...Expand

: 473-98-3
betulin

: 97-72-3
2-Methylpropionic anhydride

: C38H62O4

Conditions

Conditions	Yield
With dmap for 1h;	93%
With dmap In dichloromethane for 1h;	93%

: 55-22-1
pyridine-4-carboxylic acid

: 473-98-3
betulin

: betulin 3β,28-di-O-isonicotinate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 22℃; for 24h; regioselective reaction;	93%

: 108-30-5
succinic acid anhydride

: 473-98-3
betulin

: 3,28-dihydroxylupan bis(hydrogen succinate)

Conditions

Conditions	Yield
With pyridine for 15h; Addition; Heating;	92%
With pyridine for 8h; Reflux;	92%
Stage #1: succinic acid anhydride; betulin With pyridine; dmap for 12h; Heating / reflux; Stage #2: With hydrogenchloride In water; ethyl acetate	67%

: 473-98-3
betulin

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 212708-99-1
O,O'-bis-(trimethylsilyl)-betulin

Conditions

Conditions	Yield
With phosphomolybdic acid In chloroform for 0.833333h; Heating;	92%

Betulin Specification

The CAS registry number of Betulin is 473-98-3. The IUPAC name is (3β)-lup-20(29)-ene-3,28-diol. Its EINECS registry number is 7-475-5. In addition, the molecular formula is C₃₀H₅₀O₂ and the molecular weight is 442.7168. It belongs to the classes of Pentacyclic Triterpenes and Tri-Terpenoids. And it is an abundant naturally occurring triterpene. What's more, it can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself. It should be stored in a cool, ventilated and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 8.61; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8.607; (4)ACD/LogD (pH 7.4): 8.607; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 1145754.5; (8)ACD/KOC (pH 7.4): 1145754.5; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 40.46 Å²; (13)Index of Refraction: 1.525; (14)Molar Refractivity: 133.301 cm³; (15)Molar Volume: 435.12 cm³; (16)Polarizability: 52.845 ×10^-24cm³; (17)Surface Tension: 36.992 dyne/cm; (18)Density: 1.017 g/cm³; (19)Flash Point: 210.873 °C; (20)Enthalpy of Vaporization: 91.556 kJ/mol; (21)Boiling Point: 522.275 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. During using it, you should wear suitable protective clothing and gloves. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)CO
(2)InChI: InChI=1/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
(3)InChIKey: FVWJYYTZTCVBKE-ROUWMTJPBQ

Product Name

Betulin

Synthetic route

Betulin Specification

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