CAS 484-20-8 Bergapten - Materials / Alfa Chemistry

NAVIGATION

Bergapten

PRICE INQUIRY

Catalog Number

ACM484208-1

CAS Number

484-20-8

Product Name

Bergapten

Category

Other Materials

Synonyms

2-g)(1)benzopyran-7-one,4-methoxy-7h-furo(;4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one;4-methoxy-7H-furo[3,2-g][1]benzopyran-7-one;4-Methoxy-7H-furo[3,2-g]chromen-7-one;4-Methoxy-furo[3,2-g]chromen-7-one;5-Methoxy-6,7-furanocoumarin;6-Hydroxy-4-methoxy-5-

Description

Grayish-white microcrystalline powder or yellow fluffy solid. (NTP, 1992);Solid

IUPAC Name

4-methoxyfuro[3,2-g]chromen-7-one

Molecular Weight

216.19

Molecular Formula

C12H8O4

Canonical SMILES

COC1=C2C=CC(=O)OC2=CC3=C1C=CO3

InChI

InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3

InChI Key

BGEBZHIAGXMEMV-UHFFFAOYSA-N

Melting Point

370 °F (sublimes) (NTP, 1992);188.0 °C;188 °C (sublimes);188°C

Solubility

less than 1 mg/mL at 66° F (NTP, 1992);In water, 5 ug/mL;Practically insoluble in boiling water;Slightly soluble in glacial acetic acid, chloroform, benzene, warm phenol; soluble in absolute alcohol: 1 part in 60

Application

Bergapten is a crystalline solid psoralen derived from citrus essential oils, particularly found in bergamot. It is a 5-methoxyfurocoumarin with unique properties due to its substitution by a methoxy group at position 5. Present across various parts of Rutaceae, Umbelliferae, and leguminous plants such as ephedra, fennel, and vetch, bergapten exhibits several biological activities. It interacts with skin to exhibit phototoxic effects, possesses anticoagulant properties by counteracting heparin, demonstrates antimicrobial activity, and can effectively eliminate soft-bodied organisms. Additionally, bergapten has shown promise in dermatological treatments, notably by stimulating melanin production and enhancing skin pigmentation, making it particularly useful in the treatment of conditions like vitiligo and psoriasis.

Color/Form

Needles from alcohol

Complexity

325

Covalently-Bonded Unit Count

EC Number

207-604-5

Exact Mass

216.042259g/mol

Formal Charge

Heavy Atom Count

Log P

1.93 (LogP);log Kow = 2.0

MeSH Entry Terms

5 Methoxy Psoralen;5 Methoxypsoralen;5-Methoxy Psoralen;5-methoxypsoralen;bergapten;Pentaderm

Monoisotopic Mass

216.042259g/mol

NSC Number

755877;95437

Other Experimental

Henry's Law constant = 4.0X10-8 atm-cu m/mol at 25 °C (est);Hydroxyl radical reaction rate constant = 1.06X10-10 cu cm/molecule-sec at 25 °C (est);Ozone reaction rate constant = 2.1X10-17 cu cm/mole-sec at 25 °C (est)

Rotatable Bond Count

Stability

Stable under recommended storage conditions.

UNII

4FVK84C92X

UN Number

1759

Vapor Pressure

7.5X10-7 mm Hg at 25 °C (est)

XLogP3

2.3

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