| Identification | Back Directory | [Name]
(BETA,BETA-DIMETHYLACRYL)SHIKONIN | [CAS]
24502-79-2 | [Synonyms]
BATA
dmask
Isoarnebin I
Senecioylshikonin
Dimethylacrylshikonin
b,b-DiMethylacrylshikonin
(β,β-Dimethylacry)shikonin
(+)-yl)-4-methyl-3-pentenyleste
(BETA,BETA-DIMETHYLACRYL)SHIKONIN
(beta,beta-Dimethylacryl)shikonine
SHIKONIN-BETA,BETA-DIMETHYLACRYLATE
2-butenoicacid,3-methyl-,1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalen
(β,β-Dimethylacryl)shikonin, 98%, from Lithospermum erythrorhizon Sieb. & Zucc.
5,8-DIHYDROXY-2-[1-(BETA,BETA-DIMETHYLACRYLOYLOXY)-4-METHYL-3-PENTENYL]-1,4-NAPHTHALENEDIONE
(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate
(+)-3-Methyl-2-butenoic acid 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methyl-3-pentenyl ester
3-Methyl-2-butenoic acid (R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methyl-3-pentenyl ester
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 | [Molecular Formula]
C21H22O6 | [MDL Number]
MFCD00143687 | [MOL File]
24502-79-2.mol | [Molecular Weight]
370.4 |
| Chemical Properties | Back Directory | [Melting point ]
103°C | [Boiling point ]
587.3±50.0 °C(Predicted) | [density ]
1.269 | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO (Slightly, Sonicated), Chloroform (Slightly), Methanol (Slightly, Sonicated | [form ]
Solid | [pka]
7.07±0.20(Predicted) | [color ]
Very Dark Red to Very Dark Brown | [Stability:]
Air Sensitive, Light Sensitive | [InChIKey]
BATBOVZTQBLKIL-QGZVFWFLSA-N | [LogP]
3.130 (est) | [CAS DataBase Reference]
24502-79-2 |
| Hazard Information | Back Directory | [Uses]
(β, β-Dimethylacryl)shikonin is a useful compound in the discovery and study of FFA4 agonists from Arnebia euchroma. | [Definition]
ChEBI: Beta,beta-Dimethylacrylshikonin is a hydroxy-1,4-naphthoquinone. | [Biological Activity]
β,β-Dimethylacrylshikonin (Arnebin-1) is a main active naphthoquinone from herbal plants Lithospermum erythrorhizon (Zicao) and Arnebia euchroma th at 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-f at diet in rats. | [in vivo]
β,β-Dimethylacrylshikonin (0.1% suspension in PBS, applied topically on wounds, daily for 12d) accelerates Hydrocortisone (HY-N0583)-induced impaired wound healing in rats[2].
β,β-Dimethylacrylshikonin (1 or 2 mg/kg, i.p., on alternate days) suppresses tumor growth in BT-549 xenograft mice model by inhibiting STAT3 phosphorylation[3].
β,β-Dimethylacrylshikonin (0.5-1.5 mg/kg, i.p.) suppresses tumor growth in MFC gastric xenograft mice model[4].
| Animal Model: | Hydrocortisone induced impaired wound healing in cutaneous punch wound rat model[1] | | Dosage: | 0.1% suspension in PBS; Hydrocortisone (30?mg/kg, i.m., daily, 11d) | | Administration: | applied topically on wounds, daily for 11?days | | Result: | HE staining: Showed more number of cells and vessels in the granulation tissue, and enhanced epidermal regeneration and collagen synthesis.
Enhanced the formation and migration of the epidermis over the wound.
Increased gap closure during normal and impaired healing |
| Animal Model: | Athymic BALB/c nu/nu female mice (6- 8 week-old, 18-22 g), BT-549 cells were injected subcutaneously into the right thigh root of mice[3]. | | Dosage: | 1 or 2 mg/kg | | Administration: | i.p., on alternate days | | Result: | Decreased the expression of Ki67, CyclinB1 and CDK1 in tumor.
Up-regulated Bax expression and down-regulated Bcl-2 expression.
Increased the expression of E-cadherin and decreased N-cadherin and vimentin.
Decreased the level of p-STAT3 without changing total STAT3 levels.
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