Product Name

  • Name

    Tomatidine hydrochloride

  • EINECS
  • CAS No. 6192-62-7
  • Density
  • Solubility
  • Melting Point 281-284°C (dec.)
  • Formula C27H46ClNO2
  • Boiling Point 551.1 °C at 760 mmHg
  • Molecular Weight 452.11
  • Flash Point 287.1 °C
  • Transport Information
  • Appearance
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 6192-62-7 (Tomatidine hydrochloride)
  • Hazard Symbols
  • Synonyms (3beta,5alpha,22beta,25S)-Spirosolan-3-ol hydrochloride;
  • PSA 41.49000
  • LogP 6.49760

Synthetic route

tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

N-formyl tomatidine
1393727-99-5

N-formyl tomatidine

Conditions
ConditionsYield
Stage #1: tomatidine hydrochloride; formyl acetic anhydride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 0.25h;
Stage #2: With sodium hydrogencarbonate In ethanol; water for 168h;		79%
Stage #1: tomatidine hydrochloride; formyl acetic anhydride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: In ethanol at 20℃; for 168h; pH=9.5; Inert atmosphere;		79%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 0.25h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

tert-butyl ((S)-4-((2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-4-hydroxy-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’,1’:4,5]indeno[2,1-b]furan-10-yl)-2-methylbutyl)carbamate

tert-butyl ((S)-4-((2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-4-hydroxy-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’,1’:4,5]indeno[2,1-b]furan-10-yl)-2-methylbutyl)carbamate

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 50℃; for 18h;76%
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C32H53NO4

C32H53NO4

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 18h;75%
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

methyl chloroformate
79-22-1

methyl chloroformate

C29H47NO4

C29H47NO4

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 18h;73%
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

C27H49NO2

C27H49NO2

Conditions
ConditionsYield
With potassium hydroxide; hydrazine In ethylene glycol at 100 - 200℃; for 5h;54%
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

C27H47NO2*ClH

C27H47NO2*ClH

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen; acetic acid at 20℃; under 10343.2 Torr;54%
acetic anhydride
108-24-7

acetic anhydride

tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-acetamido-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’,1’:4,5]indeno[2,1-b]furan-4-yl acetate
2857-74-1

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-acetamido-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’,1’:4,5]indeno[2,1-b]furan-4-yl acetate

Conditions
ConditionsYield
With pyridine at 20℃; for 18h;16%
acetic anhydride
108-24-7

acetic anhydride

tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

A

3β,16β-diacetoxy-28-acetyl-16,28-seco-solanid-22-ene
23031-63-2, 61950-68-3, 124222-99-7

3β,16β-diacetoxy-28-acetyl-16,28-seco-solanid-22-ene

B

3α-acetoxy-N-acetyltomatidine
1181-86-8

3α-acetoxy-N-acetyltomatidine

Conditions
ConditionsYield
With pyridine at 20℃; for 16h;A 9%
B 9%
...Expand
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3α-acetoxy-N-formyl-tomatidine
1393728-00-1

3α-acetoxy-N-formyl-tomatidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
1.2: 168 h
2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3-α-hydroxytomatidine hydrochloride
1393728-01-2

3-α-hydroxytomatidine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
1.2: 168 h
2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C
3.1: hydrogenchloride; water / ethanol / 3 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C
3: hydrogenchloride / ethanol; water / 3 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

N-formyl-3-oxotomatidine
1393728-02-3

N-formyl-3-oxotomatidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
1.2: 168 h
2.1: Dess-Martin periodane / dichloromethane
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 3407 / 168 h / 20 °C / pH 9.5 / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3-oxotomatidine hydrochloride
1393728-03-4

3-oxotomatidine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
1.2: 168 h
2.1: Dess-Martin periodane / dichloromethane
3.1: hydrogenchloride; water / ethanol / 2 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: hydrogenchloride / ethanol; water / 2 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3β-allyloxy-N-formyltomatidine
1393728-24-9

3β-allyloxy-N-formyltomatidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
1.2: 168 h
2.1: 1,3-bis-(diphenylphosphino)propane; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 6 h / 65 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: tris-(dibenzylideneacetone)dipalladium(0); 1,3-bis-(diphenylphosphino)propane / tetrahydrofuran / 6 h / 65 °C / Inert atmosphere
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3β-allyloxytomatidine hydrochloride
1393728-25-0

3β-allyloxytomatidine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
1.2: 168 h
2.1: 1,3-bis-(diphenylphosphino)propane; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 6 h / 65 °C / Inert atmosphere
3.1: hydrogenchloride; water / ethanol / 1 h / 65 °C
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: tris-(dibenzylideneacetone)dipalladium(0); 1,3-bis-(diphenylphosphino)propane / tetrahydrofuran / 6 h / 65 °C / Inert atmosphere
3: acetyl chloride / methanol / 1 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

C27H46N2O*2ClH

C27H46N2O*2ClH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: acetic acid; ammonium acetate; sodium cyanoborohydride / methanol / pH 6 / Reflux
4: acetyl chloride / methanol / 1 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

(25S)-26-acetylamino-3β,16β,20-trihydroxy-5α-cholestane
1613158-64-7

(25S)-26-acetylamino-3β,16β,20-trihydroxy-5α-cholestane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 16 h / 20 °C
2: acetic acid; hydrogenchloride / water / 1 h / 20 °C
3: lithium borohydride / tetrahydrofuran; methanol / 0 - 20 °C
4: acetyl chloride / methanol / 1 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

N-formyl-3-aminotomatidine
1613158-52-3

N-formyl-3-aminotomatidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: acetic acid; ammonium acetate; sodium cyanoborohydride / methanol / pH 6 / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

N-formyl-3-(N-Boc-2-aminoethyl)aminotomatidine
1613158-54-5

N-formyl-3-(N-Boc-2-aminoethyl)aminotomatidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: sodium cyanoborohydride / methanol / pH 6 / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 3407 / 168 h / 20 °C / pH 9.5 / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere
3.1: sodium cyanoborohydride / methanol / pH 6 / Reflux; Inert atmosphere
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3-(N-2-aminoethyl)aminotomatidine trihydrochloride

3-(N-2-aminoethyl)aminotomatidine trihydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: sodium cyanoborohydride / methanol / pH 6 / Reflux
4: acetyl chloride / methanol / 1 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

N-formyl-3-(N-Boc-4-aminobutyl)aminotomatidine
1613158-56-7

N-formyl-3-(N-Boc-4-aminobutyl)aminotomatidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: sodium cyanoborohydride / methanol / pH 6 / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3-(N-4-aminobutyl)aminotomatidine trihydrochloride

3-(N-4-aminobutyl)aminotomatidine trihydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: sodium cyanoborohydride / methanol / pH 6 / Reflux
4: acetyl chloride / methanol / 1 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

N-formyl-3-(N-6-aminohexyl)aminotomatidine
1613158-58-9

N-formyl-3-(N-6-aminohexyl)aminotomatidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: sodium cyanoborohydride / methanol / pH 6 / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3-(N-6-aminohexyl)-aminotomatidine hydrochloride

3-(N-6-aminohexyl)-aminotomatidine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h
2: Dess-Martin periodane / dichloromethane / 20 °C
3: sodium cyanoborohydride / methanol / pH 6 / Reflux
4: acetyl chloride / methanol / 1 h / Reflux
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

(25S)-26-acetylamino-3β,16β-diacetoxy-5α-cholest-22-one
1613158-62-5

(25S)-26-acetylamino-3β,16β-diacetoxy-5α-cholest-22-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 16 h / 20 °C
2: acetic acid; hydrogenchloride / water / 1 h / 20 °C
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

(25S)-26-acetylamino-3β,16β-diacetoxy-22-hydroxy-5α-cholestane
1613158-63-6

(25S)-26-acetylamino-3β,16β-diacetoxy-22-hydroxy-5α-cholestane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 16 h / 20 °C
2: acetic acid; hydrogenchloride / water / 1 h / 20 °C
3: lithium borohydride / tetrahydrofuran; methanol / 0 - 20 °C
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

N-formyl-3-aminotomatidine

N-formyl-3-aminotomatidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 3407 / 168 h / 20 °C / pH 9.5 / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere
3.1: ammonium acetate; acetic acid; sodium cyanoborohydride / methanol / pH 6 / Reflux; Inert atmosphere
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

3-(N-aminoethyl)aminotomatidine hydrochloride

3-(N-aminoethyl)aminotomatidine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 3407 / 168 h / 20 °C / pH 9.5 / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere
3.1: sodium cyanoborohydride / methanol / pH 6 / Reflux; Inert atmosphere
4.1: acetyl chloride / methanol / 1 h / Reflux; Inert atmosphere
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-amino-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’,1’:4,5]indeno[2,1-b]furan-4-ol hydrochloride

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-amino-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’,1’:4,5]indeno[2,1-b]furan-4-ol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / 1,4-dioxane / 18 h / 50 °C
2: hydrogenchloride / 1,4-dioxane / 0.5 h
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-((tert-butoxycarbonyl)amino)-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’, 1’:4,5]indeno[2,1-b]furan-4-yl acetate acetate

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-((tert-butoxycarbonyl)amino)-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’, 1’:4,5]indeno[2,1-b]furan-4-yl acetate acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / 1,4-dioxane / 18 h / 50 °C
2: triethylamine / tetrahydrofuran / 18 h
View Scheme
tomatidine hydrochloride
6192-62-7

tomatidine hydrochloride

C30H51NO2

C30H51NO2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / 1,4-dioxane / 18 h / 50 °C
2: hydrogenchloride / 1,4-dioxane / 0.5 h
3: sodium cyanoborohydride / methanol
View Scheme

Tomatidine hydrochloride Specification

The Tomatidine hydrochloride, with the CAS registry number of 6192-62-7, is also known as (3beta,5alpha,22beta,25S)-Spirosolan-3-ol hydrochloride. It belongs to the product categories of Intermediates & Fine Chemicals; Pharmaceuticals; Steroids; Lipid signaling. This chemical's molecular formula is C27H46ClNO2 and molecular weight is 452.11. What's more, its systematic name is (3β,5α,8ξ,9ξ,14ξ)-Spirosolan-3-ol hydrochloride. In addition, it must be stored in airtight containers and placed in a dry, cool place. The dust of this chemical can not be breathed. And you should avoid contacting with skin and eyes.

Physical properties about the Tomatidine hydrochloride are: (1)ACD/LogP: 6.15; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.28; (4)ACD/LogD (pH 7.4): 4.79; (5)ACD/BCF (pH 5.5): 37.82; (6)ACD/BCF (pH 7.4): 1224.52; (7)ACD/KOC (pH 5.5): 71.9; (8)ACD/KOC (pH 7.4): 2328.2; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 21.7 Å2; (13)Flash Point: 287.1 °C; (14)Enthalpy of Vaporization: 95.56 kJ/mol; (15)Boiling Point: 551.1 °C at 760 mmHg; (16)Vapour Pressure: 1.93E-14 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: Cl.O[C@H]6CC[C@@]5(C)[C@@H](CCC3C5CC[C@@]4([C@@H]2[C@@H](O[C@]1(NCC(CC1)C)[C@H]2C)CC34)C)C6
(2) InChI: InChI=1/C27H45NO2.ClH/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4;/h16-24,28-29H,5-15H2,1-4H3;1H/t16?,17-,18-,19-,20?,21?,22?,23-,24-,25-,26-,27-;/m0./s1
(3) InChIKey: SXXHVPYRDFJKPG-JCZRXURQBN

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