Acetylshikonin

HCID 479501
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Basic information

CAS
24502-78-1
Standard SMILES
CC(=O)O[C@H](CC=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O
InChIKey
WNFXUXZJJKTDOZ-OAHLLOKOSA-N
Molecular formula
C18H18O6
Average molar mass
330.3 g/mol
Monoisotopic mass
330.1103383

Overview

(R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate has been reported in Echium italicum, Onosma paniculata, and other organisms with data available.

Names & identifiers

Preferred name
Acetylshikonin
IUPAC
[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
English name
ACETYLSHIKONIN
Molecular formula
C18H18O6
Molecular weight
330.33

Names & synonyms

Acetylshikonin24502-78-1DTXSID901317360[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetateNSC-110199((1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl) acetateRefChem:915005DTXCID101747177(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl acetate(1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl) acetate1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-, (R)-1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)-
Show more names
O-AcetylshikoninNsc110199Shikonin acetateShikonin, acetyl(R)-acetyl shikoninAcetylshikonin(natural)Acetylshikonin, 10 mM in DMSO3-pentenyl]-5,8-dihydroxy-,(R)-Racemic Acetyl Shikonin Labeled d7
ST04094S3XMFCD00143538(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate2-[(1R)-1-(Acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-1,4-naphthalenedione; (R)-2-[1-(Acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-1,4-naphthalenedione; (+)-Acetate 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone; 2-[(1R)-1-(Acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy-1,4-naphthalenedione; NSC 110199;SCHEMBL219826orb1301243SCHEMBL29440557HY-N2181

Database identifiers

CAS
24502-78-1
PubChem CID
479501
DTXSID
DTXSID901317360
ChEMBL
CHEMBL403516
Nikkaji
J61.696F

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
101 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
24

Physicochemical properties

Melting point
86 °C · 86°C
Boiling point
553.2 · 553.2±50.0 °C(Predicted)
Density
1.326 · 1.326±0.06 g/cm3(Predicted)
storage temp.
4 °C, · 4°C, protect from light
solubility
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form
Powder

Safety & regulation

Safety data

Toxicity
mouse,LD50,intraperitoneal,41mg/kg (41mg/kg),BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)BEHAVIORAL: ATAXIA,Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 73, Pg. 193, 1977.
risk_code
36/37/38
safety_code
26-36/37/39

Chemistry & industry

Applications · 1 item

UsesAcetylshikonin is the main ingredient of Zicao, which has used in clinics as a traditional Chinese for thousands of years. It exerts anti-obesity and anti-NAFLD effects through the regulation of lipid metabolism and anti-inflammatory effects. Also, it is a 1,4-naphthoquinone pigment extracted from the roots of Lithospermum erythrorhizon with anti-tumor effects.

Suppliers100 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]

Related reactions

1 records
New reaction record

Compound notes

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