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

• ChemBase ID: 127560
• Molecular Formular: C17H26O4
• Molecular Mass: 294.38594
• Monoisotopic Mass: 294.18310931
• SMILES: O=C(C[C@@H](O)CCCCC)CCc1cc(OC)c(O)cc1
• Canonical SMILES: CCCCC[C@@H](CC(=O)CCc1ccc(c(c1)OC)O)O
• InChI: 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
• InChIKey: NLDDIKRKFXEWBK-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
• IUPAC Traditional name: gingerol
• Synonyms: 3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-; 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; 6-Gingerol; [6]-Gingerol; (+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; (5S)-[6]-Gingerol; (S)-(+)-[6]Gingerol; (S)-[6]Gingerol; [6]-Gingerol; (+)-[6]-Gingerol; (5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; (S)-(+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; Gingerol; 5-羟基-1-(4-羟基-3-甲氧基苯基)-3-癸酮; 6-姜辣醇; 姜辣素; 6-姜酚

Database IDs

• CAS Number: 23513-14-6
• MDL Number: MFCD00210507
• PubChem SID: 162221879
• PubChem CID: 442793
• CHEMBL: 402978
• Chemspider ID: 391126
• KEGG ID: C10462
• Unique Ingredient Identifier: 925QK2Z900
• Wikipedia Title: Gingerol

CALCULATED PROPERTIES

• Acid pKa: 9.945873
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6165044
• LogD (pH = 7.4): 3.615294
• Log P: 3.61652
• Molar Refractivity: 83.1092 cm^3
• Polarizability: 32.557247 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble1 mg/mL, clear, colorless
• Melting Point: 30-32 °C

Safety Information

• Storage Condition: protect from light; under inert gas
• RTECS: HE0757000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); ≥98% (HPLC)
• Grade: analytical standard
• Shelf Life: (expiry date on the label)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C17H26O4

DETAILS

Sigma Aldrich - G1046

Biochem/physiol Actions
Bioactive compound found in ginger (Zingiber officinale) with antioxidant activity,1 which functions as an anti-inflammatory and antitumor agent. [6]-Gingerol down regulates proinflammatory cytokine release by macrophages.2 It has been shown to inhibit COX-2 expression by blocking the activation of p38 MAP kinase and NF-κB in phorbol ester-stimulated mouse skin.3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G1046.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 50866

Biochem/physiol Actions
Bioactive compound found in ginger (Zingiber officinale) with antioxidant activity,1 which functions as an anti-inflammatory and antitumor agent. [6]-Gingerol down regulates proinflammatory cytokine release by macrophages.2 It has been shown to inhibit COX-2 expression by blocking the activation of p38 MAP kinase and NF-κB in phorbol ester-stimulated mouse skin.3

Toronto Research Chemicals - G387205

(+)-[6]-Gingerol is a bioactive compound found in ginger (Zingiber officinale) with antioxidant activity, which functions as an anti-inflammatory and antitumor agent. (+)-[6]-Gingerol down regulates proinflammatory cytokine release by macrophages. (+)-[6]

REFERENCES

• Aeschbach, R. et al.: Food Chem. Toxicol., 32, 31 (1994)
• Tripathi, S. et al.: J. Surg. Res., 130, 318 (1994)
• Kim, S.O., et al.: Oncogene 24, 2558 (1994)