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Tomatidine hydrochloride is a steroidal alkaloid that is structurally similar to Cyclopamine. However, it does not inhibit the hedgehog pathway. It is an off-white solid and is known for its protective effects against muscle atrophy and its ability to boost muscle growth.

6192-62-7

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Basic information
1. Product Name: TOMATIDINE HYDROCHLORIDE
2. Synonyms: 3BETA-HYDROXY-5ALPHA-TOMATIDANE HYDROCHLORIDE;5ALPHA-TOMATIDAN-3BETA-OL HYDROCHLORIDE;TOMATIDINE HCL;TOMATIDINE HYDROCHLORIDE;SPIRPSOLAN-3-OL-(3B,5A,22B,25C) HCL;3β-Hydroxy-5α-tomatidane hydrochloride, 5α-Tomatidan-3β-ol hydrochloride;(3beta,5alpha,22beta,25S)-Spirosolan-3-ol hydrochloride;TOMATIDINE HCL(RG)
3. CAS NO:6192-62-7
4. Molecular Formula: C27H46ClNO2
5. Molecular Weight: 452.11
6. EINECS: N/A
7. Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Lipid signaling
8. Mol File: 6192-62-7.mol
Chemical Properties
1. Melting Point: 281-284°C (dec.)
2. Boiling Point: 551.1 °C at 760 mmHg
3. Flash Point: 287.1 °C
4. Appearance: /
5. Density: N/A
6. Refractive Index: N/A
7. Storage Temp.: 2-8°C
8. Solubility: Methanol (Slightly)
9. BRN: 3920740
10. CAS DataBase Reference: TOMATIDINE HYDROCHLORIDE(CAS DataBase Reference)
11. NIST Chemistry Reference: TOMATIDINE HYDROCHLORIDE(6192-62-7)
12. EPA Substance Registry System: TOMATIDINE HYDROCHLORIDE(6192-62-7)
Safety Data
1. Hazard Codes: N/A
2. Statements: N/A
3. Safety Statements: 22-24/25
4. WGK Germany: 3
5. RTECS:
6. HazardClass: N/A
7. PackingGroup: N/A
8. Hazardous Substances Data: 6192-62-7(Hazardous Substances Data)

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6192-62-7 Usage

Uses

Used in Pharmaceutical Research:
Tomatidine hydrochloride is used as a negative control for Cyclopamine and KAAD-Cyclopamine in pharmaceutical research. This application is due to its structural similarity to Cyclopamine but without the inhibition of the hedgehog pathway.
Used in Muscle Atrophy Prevention:
Tomatidine hydrochloride is used as a protective agent against muscle atrophy. Its application in this area is based on its ability to prevent the loss of muscle mass, which can be beneficial for individuals suffering from conditions that lead to muscle wasting.
Used in Muscle Growth Enhancement:
Tomatidine hydrochloride is also used as a muscle growth enhancer. This application is due to its ability to stimulate muscle growth, which can be particularly useful for athletes and individuals looking to improve their physical performance and muscle mass.

Biological Activity

Tomatidine is a steroidal alkaloid that has been found in the skins and leaves of tomatoes. It suppresses NF-κB signaling in LPS-stimulated macrophages, blocking induced expression of inducible nitric oxide synthase (iNOS) and COX-2. Tomatidine inhibits acid sphingomyelinase activity by 84.2% when used at a concentration of 10 mM. It also has antibacterial properties, preferentially blocking the replication of S. aureus variants that are pathogenic in cystic fibrosis over normal strains (MICs = 0.12 and >16 μg/ml, respectively). It prevents skeletal muscle atrophy associated with fasting or spinal cord injury in mice. Tomatidine has also been used as a negative control for cyclopamine (Item No. 11321) in studies involving signaling mediated by the hedgehog pathway.

Mode of action

Tomatidine hydrochloride acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling. It activates autophagy either in mammal cells or C elegans.

Check Digit Verification of cas no

The CAS Registry Mumber 6192-62-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,9 and 2 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6192-62:
(6*6)+(5*1)+(4*9)+(3*2)+(2*6)+(1*2)=97
97 % 10 = 7
So 6192-62-7 is a valid CAS Registry Number.

6192-62-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name	Tomatidin Hydrochloride

1.2 Other means of identification

Product number	-
Other names	TOMATIDINE HYDROCHLORIDE

1.3 Recommended use of the chemical and restrictions on use

Identified uses	For industry use only.
Uses advised against	no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number	-
Service hours	Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6192-62-7 SDS

6192-62-7Synthetic route

: 6192-62-7
tomatidine hydrochloride

: 2258-42-6
Acetic formic anhydride

: 1393727-99-5
N-formyl tomatidine

Conditions	Yield
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;

Conditions	Yield
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

Conditions	Yield
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