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Dokumente

SML3463

Sigma-Aldrich

β,β-Dimethylacrylshikonin

≥98% (HPLC)

Synonym(e):

3-​methyl-​2-​butenoic acid (1R)​-​1-​(1,​4-​dihydro-​5,​8-​dihydroxy-​1,​4-​dioxo-​2-​naphthalenyl)​-​4-​methyl-​3-​penten-​1-​yl ester, Arnebin-1, Dimethylacrylshikonin, Dmask, [(1R)-1-(5,8-Dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate

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About This Item

Empirische Formel (Hill-System):
C21H22O6
CAS-Nummer:
24502-79-2
Molekulargewicht:
370.40
MDL-Nummer:
MFCD00143687
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

, Red to very dark purple

Löslichkeit

DMSO: 2 mg/mL, clear (Warmed)

Lagertemp.

-10 to -25°C

InChI

1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3/t17-/m1/s1

InChIKey

BATBOVZTQBLKIL-QGZVFWFLSA-N

Biochem./physiol. Wirkung

β,β-Dimethylacrylshikonin (Arnebin-1) is a main active naphthoquinone from herbal plants Lithospermum erythrorhizon (Zicao) and Arnebia euchroma that exhibits anti-neoplasm and antihyperglycemic activities. It stimulates autophagy in lung adenocarcinoma cells through activation of CaMKKβ-AMPK-mTOR pathway. β,β-Dimethylacrylshikonin facilitates wound healing through PI3K pathway. β,β-Dimethylacrylshikonin improves nonalcoholic fatty liver disease induced by a high-fat diet in rats.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Haibing Wang et al.
Biochemical and biophysical research communications, 517(3), 477-483 (2019-08-05)
β,β-Dimethylacrylshikonin (DMAS), an active ingredient of Lithospermum erythrorhizon and Arnebia euchroma, possess anti-neoplasm properties. Recently, DMAS was reported to stimulate autophagy in lung adenocarcinoma cells. However, the mechanisms by which DMAS modulates autophagy. have not yet been clearly elucidated. In
Weijia Yang et al.
The Journal of international medical research, 47(3), 1250-1263 (2019-01-27)
To examine the effects of arnebin-1 on nonalcoholic fatty liver disease (NAFLD) induced by a high-fat diet (HFD). Male Sprague-Dawley rats were fed an HFD for 10 weeks and then treated with arnebin-1 at a dose of 5, 10 or
Zhi Zeng et al.
International journal of molecular medicine, 36(3), 685-697 (2015-07-24)
Arnebin-1, a naphthoquinone derivative, plays a crucial role in the wound healing properties of Zicao (a traditional wound healing herbal medicine). It has been noted that Arnebin-1, in conjunction with vascular endothelial growth factor (VEGF), exerts a synergistic pro-angiogenic effect

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