2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

• ChemBase ID: 103371
• Molecular Formular: C15H14O3
• Molecular Mass: 242.26986
• Monoisotopic Mass: 242.09429431
• SMILES: CC(=CCC1=C(O)C(=O)c2ccccc2C1=O)C
• Canonical SMILES: CC(=CCC1=C(O)C(=O)c2c(C1=O)cccc2)C
• InChI: InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3
• InChIKey: CIEYTVIYYGTCCI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: tecomin; 2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
• Synonyms: 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone; Lapachol; 2-Hydroxy-3-[3-methyl-2-butenyl)-1,4-naphthoquinone]; Natural Yellow 16; LAPACHOL; Greenhartin; Taiguic acid; Groenhartin; Lapachoic acid; 2-羟基-3-(3-甲基-2-丁烯基)-1,4-萘醌; 黄钟花醌; 拉帕醇

Database IDs

• CAS Number: 84-79-7
• EC Number: 201-563-7
• MDL Number: MFCD00001679
• PubChem SID: 24848565; 162090374
• PubChem CID: 3884
• Color Index Number: 75490

CALCULATED PROPERTIES

• Acid pKa: 5.7291365
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.3850307
• LogD (pH = 7.4): 0.9122968
• Log P: 2.5863564
• Molar Refractivity: 71.7093 cm^3
• Polarizability: 26.409409 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow powder
• Melting Point: 141-143 °C(lit.)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: QL8750000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Mechanism of Action: Inhibitor of DNA replication and RNA synthesis

Product Information

• Purity: 98%
• Biological Source: Widespread occurrence in the plant world, particularly in heartwood, bark and roots, e.g. the Bignoniaceae and various Tabebuia, Tecomella and Tectona spp.
• Application(s): Antibacterial; Anticancer activity; Anticoagulant; Antifungal agent
• Empirical Formula (Hill Notation): C15H14O3

DETAILS

Sigma Aldrich - 142905

Packaging
250 mg in glass bottle

REFERENCES

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