Basic information
- CAS
23513-14-6- Standard SMILES
CCCCC[C@H](O)CC(=O)CCc1ccc(O)c(OC)c1- InChIKey
NLDDIKRKFXEWBK-AWEZNQCLSA-N- Molecular formula
- C17H26O4
- Average molar mass
- 294.4 g/mol
- Monoisotopic mass
- 294.18310931
Overview
Gingerol is a beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger. It has a role as an antineoplastic agent and a plant metabolite. It is a member of guaiacols and a beta-hydroxy ketone.
Names & identifiers
- Preferred name
- (6)-Gingerol
- IUPAC
- (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
- English name
- 6-Gingerol
- Molecular formula
- C17H26O4
- Molecular weight
- 294.39
Names & synonyms
6-Gingerolgingerol23513-14-6[6]-Gingerol(6)-Gingerol(S)-(+)-[6]Gingerol(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one(S)-(6)-GingerolDTXSID3041035(+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone925QK2Z900(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxy-phenyl)decan-3-one
Show more names
GingerolsGingerolumrac-(R*)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane-3-one6-CurcuminGINGEROL [6](s)-3-decanon6-Gingerol-RM
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-CHEBI:10136(S)-(+)-(6)GingerolRefChem:5858DTXCID1021035(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one(+)-[6]-Gingerol1391-73-7
Database identifiers
- CAS
23513-14-6、58253-27-3- PubChem CID
- 442793
- DTXSID
DTXSID3041035
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 10
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 293
Experimental & physicochemical properties
LipidsLipids -> Polyketides [PK] -> Phenolic lipids [PK15] -> Alkyl catechols and derivatives [PK1502]
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section169.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3041035]
Physicochemical properties
- Melting point
- 31 ℃ · 31℃
- Boiling point
- 453 · 453.0±35.0 °C(Predicted)
- Density
- 1.083 · 1.083±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 1 mg/mL, · methanol: soluble1mg/mL, clear, colorless
- form
- Pale yellow oil
- pka
- 10.02 · 10.02±0.20(Predicted)
- color
- White to Light yellow
- Major Application
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (75%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 124 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (75%)
Safety data
- wgk
- 3
- rtecs
- HE0757000
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29145090
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36/37
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses[6]-Gingerol has been used:to study its effects on transient receptor potential (TRP) channelsto study its effects on experimental models of non-alcoholic steatohepatitisto determine its effects on microsomal prostaglandine E2 synthase 1 (mPGES-1), glycogen synthase kinase 3β (GSK-3β) and β-catenin pathway in A549 cell lineto analyse the effects of 6-Shogaol (6-SG) on diabetic nephropathy (DN) in db/db mice
General Description6-Gingerol is a naturally occurring plant phenoland an active pungent constituent found in the rhizome of ginger, which is known to possess anti-inflammatory, anti-tumor and antioxidant properties and can hence, serve as a potential candidate in the treatment of cancer.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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