Basic information
- CAS
77-59-8- Standard SMILES
C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
XYNPYHXGMWJBLV-VXPJTDKGSA-N- Molecular formula
- C27H45NO2
- Average molar mass
- 415.7 g/mol
- Monoisotopic mass
- 415.34502968
Overview
Tomatidine is a 3beta-hydroxy steroid resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group. It is an azaspiro compound, a 3beta-hydroxy steroid and an oxaspiro compound. It is a conjugate base of a tomatidine(1+). It derives from a hydride of a tomatidane.
Names & identifiers
- Preferred name
- Tomatidine
- IUPAC
- (1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol
- English name
- TOMATIDINE
- Molecular formula
- C27H45NO2
- Molecular weight
- 415.65
Names & synonyms
Tomatidine77-59-8Tomatidin(3beta,5alpha,22beta,25S)-Spirosolan-3-olDTXSID0037102Spirosolan-3-ol, (3beta,5alpha,22beta,25S)-CHEBI:96292B73S48786NSC-27592NSC-226903(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-ol
Show more names
omatidineTOMATADINENSC 226903TOMATIDINE(RG)Spirosolan-3-olTomatidine, >98%high qualtiy Tomatidine5alpha-Tomatidan-3beta-ol
RefChem:190356(3 beta,5 alpha,22 beta, 25S)-spirosolan-3-olDTXCID8017102201-040-3(22S,25S)-spirosolan-3beta-olPrestwick_473(22S,25S)-5alpha-spirosolan-3beta-olPrestwick3_000573
Properties
Computed structural properties
- XLogP
- 6.2
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 696
Experimental & physicochemical properties
SpringerMaterials PropertiesCrystal structure
Physicochemical properties
- Melting point
- 210.5 ℃ · 210.5℃
- alpha
- 25 · D25 +8° (chloroform)
- Boiling point
- 534.2 °C · 534.2°C (rough estimate)
- Density
- 1.0048 · 1.0048 (rough estimate)
- refractive index
- 1.684 · 1.6840 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 2.86 mg/mL · DMSO : 2.86 mg/mL (6.88 mM);Water : < 0.1 mg/mL (insoluble)
- pka
- 15.14 · 15.14±0.70(Predicted)
- form
- Solid
- color
- White to off-white
- LogP
- 6.15 · 6.150 (est)
- FDA UNII
- 2 B73S48786 · 2B73S48786
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (50%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P270, P271, P301+P316, P301+P317, P304+P340, P316, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (50%)
Safety data
- ridadr
- 1544
- risk_code
- 23/25
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 1-45
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
UsesTomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2].
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers102 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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