[6]-Gingerol - Moligand™, 10mM in DMSO , Activator of TRPA1, CAS No.23513-14-6, Activator of TRPA1

CAS: 23513-14-6 Cat. No.: G422764 Formula: C₁₇H₂₆O₄ Molecular Weight: 294.39 EC Number: 607-241-6

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)- | HMS1361D09 | (+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone | CCG-208214 | HY-14615 | [1-(4''-hydroxy-3''-methoxyphenyl)-5-hydroxy-3-decanone] | 925QK2Z900 | AKOS006222484 | [6]-Ging

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Gingerol, a phenolic substance and a potent cardiotonic agent isolated from the rhizome of ginger, has been shown to stimulate the Ca2+-pumping activity of sarcoplasmic reticulum (SR) of rabbits in a concentration-dependent manner. It was noted that Gingerol specifically activated SERCA (Ca2+-ATPase of cardiac and skeletal SR). Additional research has shown Gingerol to inhibit platelet aggregation via suppression of thromboxane production. Gingerol blocked ATP release from platelets induced by adrenaline and adenosine 5-diphosphate and prevented secondary aggregation. It has been demonstrated that Gingerol contains antioxidant and antiinflammatory characteristics and could significantly inhibit 7,12-dimethylbenz[a]anthracene-induced skin papillomagenesis in mice. Furthermore, Gingerol has been noted as an agonist of the capsaicin-activated VR1 (vanilloid receptor) and in leukemia cell studies it has been shown to have apoptotic properties.

Specifications

Synonyms

3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)- | HMS1361D09 | (+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone | CCG-208214 | HY-14615 | [1-(4''-hydroxy-3''-methoxyphenyl)-5-hydroxy-3-decanone] | 925QK2Z900 | AKOS006222484 | [6]-Ging

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Apoptotic, antioxidant and anti-inflammatory agent. SERCA activator (EC 50 = 4 μM, Ca 2+ ATPase in cardiac sarcoplasmic reticulum). Inhibts COX-2 expression. Blocks p38 MAP kinase activation. Shows antiangiogenic effects in vivo. Orally active.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR

Mechanism of action

Activator of TRPA1

Names and Identifiers

Pubchem Sid

528762157

Canonical Smiles

CCCCCC(CC(=O)CCC1=CC(=C(C=C1)O)OC)O

IUPAC Name

(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

InChIKey

NLDDIKRKFXEWBK-AWEZNQCLSA-N

INCHI

1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1

Isomeric SMILES

CCCCC[C@@H](CC(=O)CCC1=CC(=C(C=C1)O)OC)O

WGK Germany

3

RTECS

HE0757000

UN Number

2811

Molecular Weight

294.39

Reaxy-Rn

2059333

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2059333&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenols
      • Subclass Methoxyphenols

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenols
• Subclass: Methoxyphenols
• Intermediate Tree Nodes: Not available
• Direct Parent: Gingerols
• Alternative Parents: Fatty alcohols Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Beta-hydroxy ketones Secondary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Gingerol - Fatty alcohol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Beta-hydroxy ketone - Fatty acyl - Ketone - Secondary alcohol - Ether - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Alcohol - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as gingerols. These are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.
• External Descriptors: Zingiber derived compounds

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (0 Activities)

Discover Target: TRPA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Sensitivity: Light ＆ heat sensitive.
• Molecular Weight: 294.400 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 294.183 Da
• Monoisotopic Mass: 294.183 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 293.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1