2,3-Epoxy-2-methyl-1,4-naphthoquinone

HCID 85845

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Basic information

CAS: 15448-59-6
Standard SMILES: CC12OC1C(=O)c1ccccc1C2=O
InChIKey: NNUKDUBCRRYXDC-UHFFFAOYSA-N
Molecular formula: C11H8O3
Average molar mass: 188.18 g/mol
Monoisotopic mass: 188.04734412

Names & identifiers

Preferred name: 2,3-Epoxy-2-methyl-1,4-naphthoquinone
IUPAC: 1a-methyl-7aH-naphtho[2,3-b]oxirene-2,7-dione
English name: Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl- (9CI)
Molecular formula: C11H8O3
Molecular weight: 188.18

Names & synonyms

Menadione epoxide15448-59-6Menadione-2,3-epoxideMenadione oxideVitamin K3 2,3-oxideNSC 656692,3-epoxy-2-methyl-1,4-naphthoquinoneRefChem:908668Menadione 2,3-Epoxide1a-methyl-7aH-naphtho[2,3-b]oxirene-2,7-dione2,3-Epoxy-2,3-dihydro-2-methyl-1,4-naphthoquinone1a-Methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione

Show more names

VitaminK1Impurity7Phytonadione ImpurityVitamin K3 2,3-epoxideVitamin K1 Impurity 19Phytonadione Impurity 19

1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-2-Methyl-2,3-epoxy-2,3-dihydro-1,4-naphthoquinoneNaphth(2,3-b)oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-DTXSID80934995NSC-65669Vitamin K1 Impurity 30Vitamin K1 Impurity 95

Database identifiers

CAS: 15448-59-6
PubChem CID: 85845
DTXSID: DTXSID80934995
ChEMBL: CHEMBL3220796
Nikkaji: J103.791I

Properties

Computed structural properties

XLogP: 1.2
Topological polar surface area: 46.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 322

Physicochemical properties

Melting point: 100 · 100-101 °C
Boiling point: 357.4 · 357.4±42.0 °C(Predicted)
Density: 1.406 · 1.406±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
form: powder
color: white
BRN: 144630 · 144630
Major Application: cell analysis
InChI: 1S/C11H8O3/c1-11-9(13)7-5-3-2-4-6(7)8(12)10(11)14-11/h2-5,10H,1H3
InChIKey: NNUKDUBCRRYXDC-UHFFFAOYSA-N
SMILES: O=C1C2(C)C(O2)C(C3=CC=CC=C31)=O
UNSPSC Code: 12352200 · 12352200
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Danger
Hazard statements: 335 · H335-H317-H334-H319-H315
Precautionary statements: 261 · P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P280-P302+P352-P321-P332+P313-P362-P261-P285-P304+P341-P342+P311-P501-P264-P280-P305+P351+P338-P337+P313P
WGK Germany: 3 · WGK 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

wgk: WGK 3
Signal word: Danger
Symbol(GHS): GHS07,GHS08
Storage Class: 11 - Combustible Solids
Hazard statements: H335-H317-H334-H319-H315
Precautionary statements: P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P280-P302+P352-P321-P332+P313-P362-P261-P285-P304+P341-P342+P311-P501-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Applications

UsesMenadione 2,3-Epoxide is a Vitamin K derivative found to induce selective tumor cytotoxicty in neublastoma as well as induce apotosis through activiation of ROS-dependent ERK and JNK protein phosphorylation.