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[8]-Gingerol

$330

  • Brand : BIOFRON

  • Catalogue Number : AV-P10890

  • Specification : 98%

  • CAS number : 23513-08-8

  • Formula : C19H30O4

  • Molecular Weight : 322.44

  • PUBCHEM ID : 168114

  • Volume : 0.2mL

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Catalogue Number

AV-P10890

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

322.44

Appearance

White waxy solid

Botanical Source

Pueraria lobata (Willd.) Ohwi/ginger (Zingiber officinale)

Structure Type

Phenols

Category

Standards;Natural Pytochemical;API

SMILES

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

Synonyms

8-Gingerol/(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone/3-Dodecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-/(5s)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one/(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone

IUPAC Name

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

Applications

8-Gingerol, found in the rhizomes of ginger (Z. officinale) with oral bioavailability, activates TRPV1, with an EC50 of 5.0 ?M. 8-Gingerol inhibits COX-2, and inhibits the growth of H. pylori in vitro[1][2].

Density

1.1±0.1 g/cm3

Solubility

Methanol

Flash Point

162.6±19.4 °C

Boiling Point

476.4±35.0 °C at 760 mmHg

Melting Point

30 - 32 °C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:23513-08-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

23892040

Abstract

[8]-Gingerol is an active component of Zinger and shows several pharmacological activities, such as antipyretic and anti-inflammation characteristics. To identify a potential skin-whitening agent, the inhibitory effects of [8]-gingerol on melanogenesis and its mechanism of action were investigated. In the present study, the effects of [8]-gingerol on mushroom tyrosinase, tyrosinase activity and melanin content were determined spectrophotometrically; the expression of melanogenesis-related proteins in B16F10 and B16F1 melanoma cells were determined by Western blotting. Furthermore, the possible signaling pathways involved in [8]-gingerol-mediated depigmentation were also investigated using specific inhibitors. The results revealed that [8]-gingerol (5-100μM) effectively suppressed intracellular tyrosinase activity and decreased the amount of melanin in B16F10 and B16F1 cells. In addition, [8]-gingerol also effectively decreased intracellular reactive species (RS) and reactive oxygen species (ROS) levels at the same dose range. Our results indicated that [8]-gingerol inhibited melanogenesis in B16F10 and B16F1 cells by down-regulation of both mitogen-activated protein kinases (MAPK) and protein kinase A (PKA) signaling pathways or through its antioxidant properties. Hence, [8]-gingerol could be used as an effective skin-whitening agent.

KEYWORDS

Melanin; Melanogenesis; Tyrosinase; [8]-Gingerol.

Title

[8]-Gingerol Inhibits Melanogenesis in Murine Melanoma Cells Through Down-Regulation of the MAPK and PKA Signal Pathways

Author

Huey-Chun Huang 1 , Yin-Chun Chou, Chia-Yin Wu, Tsong-Min Chang

Publish date

2013 Aug 23

PMID

28762585

Abstract

Ulcerative colitis is one of the most common types of inflammatory bowel disease and is multifactorial and relapsing. 6-Gingerol, a component of gingerols extracted from ginger (Zingiber officinale), has been reported to improve ulcerative colitis. The present study aims to investigate the therapeutic efficacy of two analogous forms of 6-gingerol, 8-gingerol, and 10-gingerol, on ulcerative colitis. Colitis was induced in rats through consumption of 5% (w/v) dextran sulfate sodium drinking water for 7 consecutive days. 6-Gingerol, 8-gingerol, and 10-gingerol were then given intraperitoneally at doses of 30 mg kg-1 d-1 for another 7 days, respectively. Body weight change, disease activity index, inflammatory cytokines, and oxidative stress indices were measured, and the colonic tissue injuries were assessed macroscopically and histopathologically. Results showed that all three gingerols attenuated colitic symptoms evoked by dextran sulfate sodium, significantly elevated superoxide dismutase activity, decreased malondialdehyde levels and myeloperoxidase activity in the colon tissue, and markedly reduced the content of tumor necrosis factor alpha and Interleukin 1 beta in the serum. Histological observations showed that all three gingerols obviously accelerated mucosal damage healing. It is concluded that 6-gingerol, 8-gingerol, and 10-gingerol, the three analogues, have a strong and relatively equal efficacy in the treatment of colitis. Copyright ? 2017 John Wiley & Sons, Ltd.

KEYWORDS

Melanin; Melanogenesis; Tyrosinase; [8]-Gingerol.

Title

Therapeutic Effects of 6-Gingerol, 8-Gingerol, and 10-Gingerol on Dextran Sulfate Sodium-Induced Acute Ulcerative Colitis in Rats

Author

Feng Zhang 1 , Na Ma 1 , Yong-Feng Gao 1 , Li-Li Sun 1 , Ji-Guo Zhang 1

Publish date

2017 Sep

PMID

26178781

Abstract

[6]-Gingerol, [8]-gingerol, and [10]-gingerol are pungent components of fresh ginger, extracts of which inhibit various components of the inflammatory response. Because little is known regarding the effect of gingerols with different unbranched alkyl side chain lengths on the activation and effector function of T lymphocytes, we compared the effects of [6]-gingerol, [8]-gingerol, and [10]-gingerol on murine T lymphocyte proliferation, expression of CD25 and CD69 activation markers, cytokine synthesis, and interleukin (IL)-2 receptor signaling. All three gingerols inhibited DNA synthesis by T lymphocytes, as well as interferon-γ synthesis. In contrast, only [8]-gingerol and [10]-gingerol inhibited CD25 and CD69 expression, and IL-2 synthesis. None of the gingerols affected IL-4 synthesis. Exogenous IL-2 enhanced T lymphocyte proliferation in the presence of [6]-gingerol but did not significantly increase T lymphocyte proliferation in the presence of [8]-gingerol or [10]-gingerol. In line with this finding, [8]-gingerol and [10]-gingerol impaired IL-2-induced proliferation of CTLL-2 cells, but constitutive CD25 expression was unaffected, indicating inhibition of IL-2 receptor signaling. In general, [10]-gingerol and [8]-gingerol were more potent inhibitors of T lymphocytes than [6]-gingerol. Suppression of T lymphocyte responses by gingerols suggests that these phytochemicals may be beneficial in chronic inflammatory conditions associated with excessive or inappropriate T lymphocyte activation.

Title

Differential Inhibition of T Lymphocyte Proliferation and Cytokine Synthesis by [6]-Gingerol, [8]-Gingerol, and [10]-Gingerol

Author

Megan Bernard 1 , Suzanne J Furlong 1 , Melanie R Power Coombs 1 , David W Hoskin 1 2 3

Publish date

2015 Nov