Skip to Content
MilliporeSigma

Key Documents

View All Documentation

SML3463

β,β-Dimethylacrylshikonin

≥98% (HPLC)

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C21H22O6
CAS Number:
24502-79-2
Molecular Weight:
370.40
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00143687
Assay:
≥98% (HPLC)
Form:
powder
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Segment

100

assay

≥98% (HPLC)

form

powder

color

, Red to very dark purple

solubility

DMSO: 2 mg/mL, clear (Warmed)

storage temp.

-10 to -25°C

SMILES string

O([C@H](CC=C(C)C)C1=CC(=O)c2c(c(ccc2O)O)C1=O)C(=O)C=C(C)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

InChI key

BATBOVZTQBLKIL-QGZVFWFLSA-N

Biochem/physiol Actions

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.
Anti-neoplasm and antihyperglycemic; facilitates wound healing through PI3K pathway.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library