Basic information
- CAS
517-88-4- Standard SMILES
CC(C)=CCC(O)C1=CC(=O)c2c(O)ccc(O)c2C1=O- InChIKey
NEZONWMXZKDMKF-UHFFFAOYSA-N- Molecular formula
- C16H16O5
- Average molar mass
- 288.29 g/mol
- Monoisotopic mass
- 288.09977361
Overview
C.I. Natural Red 20 is a naphthoquinone.
Names & identifiers
- Preferred name
- (+-)-Shikonin
- IUPAC
- 5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
- English name
- Shikalkin
- Molecular formula
- C16H16O5
- Molecular weight
- 288.3
Names & synonyms
54952-43-1(+-)-ShikoninRefChem:905516SHIKALKIN(Rac)-ShikoninC.I. Natural Red 205,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione(+/-)-ShikoninARNEBIN-45,8-DIHYDROXY-2-(1-HYDROXY-4-METHYLPENT-3-EN-1-YL)NAPHTHALENE-1,4-DIONE(+/-)-AlkanninMFCD00016668
Show more names
shiconinNsc 291845Shikonin >=98% (HPLC)Shikonin (mixture of optical isomers, about 1:1)
23444-65-7KBioGR_000610C.I. 75530KBio3_001080BDBM178090HY-N6004NSC94524NSC252844
Database identifiers
- CAS
517-88-4、517-89-5、54952-43-1、85251-58-7- PubChem CID
- 5208
- ChEMBL
CHEMBL29285- ChEBI
CHEBI:174748- EC Number
- 286-469-4、684-467-1
- Nikkaji
- J20.957K
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 501
Experimental & physicochemical properties
CosmeticsTonic
Food AdditivesUse unspecified -> FDA Substance added to food
Melting Point116 - 117 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 144 · 144-145 °C
- Boiling point
- 567.4 · 567.4±50.0 °C(Predicted)
- Density
- 1.373 · 1.373±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 1 mg/mL · methanol: soluble1mg/mL
- form
- powder or solid
- pka
- 7.34 · 7.34±0.20(Predicted)
- color
- red to brown
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- risk_code
- 22-50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xn,N
- safety_code
- 61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H400
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1
- Precautionary statements
- P273-P301+P312+P330
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Cellular LocationsCytoplasm
Uses & manufacturing
Use ClassificationCosmetics -> Tonic
Applications
UsesShikonin has been used:to enhance the anti-tumor activity of gefitinib on tyrosine kinase receptor epidermal growth factor receptor (EGFR) in wild-type lung cancer cellsas an inhibitor of renal aerobic glycosis and a potentialas an anti-inflammatory agent to test its role to improve lipopolysaccharide (LPS)-induced cardiac dysfunctionto stimulate bone marrow-derived macrophages (BMDMs) to test the effect of Interferon regulatory factor 1 on cell death
General DescriptionShikonin is a major phytochemical compound extracted from the roots of Lithospermum erythrorhizon. It is a natural anthraquinone derivative.
Additional notes
DefinitionChEBI: C.I. Natural Red 20 is a naphthoquinone.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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