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Merck

39303

[6]-Shogaol

analytical standard

Synonym(s):

1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one

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About This Item

Empirical Formula (Hill Notation):
C17H24O3
CAS Number:
555-66-8
Molecular Weight:
276.37
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329755838
MDL number:
MFCD01736094
Beilstein/REAXYS Number:
2056098

Key Documents

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storage temp.

2-8°C

Quality Level

100

InChI

1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+

SMILES string

CCCCC\C=C\C(=O)CCc1ccc(O)c(OC)c1

InChI key

OQWKEEOHDMUXEO-BQYQJAHWSA-N

grade

analytical standard

assay

≥90.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

[6]-Shogaol is a pungent and one of the most abundant dehydrated form of gingerols present in the fresh ginger roots or dried and thermally treated roots. It may serve as a potential anti-inflammatory agent.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
This compound is commonly found in plants of the genus: zingiber

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

39303-VAR: + 39303-10MG: + 39303-BULK:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8779
BCCF8038
BCCD6906
BCCB7141
BCBV9116

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Huadong Chen et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 907, 126-139 (2012-10-04)
Ginger is frequently consumed as a spice and has numerous medicinal properties. Extensive research has characterized the anti-inflammatory, antioxidant, and antitumor activities of ginger. Previously, we reported the mercapturic acid pathway as a major metabolic route of [6]-shogaol in mice
Heinz H Pertz et al.
Planta medica, 77(10), 973-978 (2011-02-10)
The herbal drug ginger (Zingiber officinale Roscoe) may be effective for treating nausea, vomiting, and gastric hypomotility. In these conditions, cholinergic M (3) receptors and serotonergic 5-HT (3) and 5-HT (4) receptors are involved. The major chemical constituents of ginger
Sehwan Shim et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(3-4), 597-602 (2011-12-07)
[6]-Shogaol has beneficial effects in spinal neuronal regeneration, but associated molecules and mechanisms are not identified. Neurotrophic factors, including brain-derived neurotrophic factor (BDNF), are associated with proliferation and differentiation of neuronal cells and exert a neuroprotective effect in neurodegenerative models.
Qingliang Qiao et al.
Journal of chromatography. A, 1218(36), 6187-6190 (2011-01-05)
The flash high speed counter-current chromatographic (FHSCCC) separation of gingerols and 6-shogaol was performed on a HSCCC instrument equipped with a 1200-ml column (5 mm tubing i.d.) at a flow rate of 25 ml/min. The performance met the FHSCCC feature
Min-Ji Bak et al.
Molecules (Basel, Switzerland), 17(7), 8037-8055 (2012-07-06)
The rhizome of ginger (Zingiber officinale Roscoe) is known to have several bioactive compounds including gingerols and shogaols which possess beneficial health properties such as anti-inflammatory and chemopreventive effects. Based on recent observations that 6-shogaol may have more potent bioactivity
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