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Merck
CN

K2750

Khellin

crystalline

Synonym(s):

4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one

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About This Item

Empirical Formula (Hill Notation):
C14H12O5
CAS Number:
82-02-0
Molecular Weight:
260.24
EC Number:
201-392-8
UNSPSC Code:
41116107
PubChem Substance ID:
24896221
Beilstein/REAXYS Number:
263185
MDL number:
MFCD00005007

Key Documents

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InChI key

HSMPDPBYAYSOBC-UHFFFAOYSA-N

InChI

1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

SMILES string

COc1c2OC(C)=CC(=O)c2c(OC)c3ccoc13

form

crystalline

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

color

light yellow

bp

180-200 °C/0.05 mmHg (lit.)

mp

150-154 °C (lit.)

format

neat

storage temp.

−20°C

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General description

Khellin is a drug, which belongs to the group of furochromones.It is isolated from a perennial plant named Ammivisnaga L, that usually grows in the mediterranean regions.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
127F0359
049F0365
043K3714
031H2502

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Total synthesis of khellin via a chromium carbene complex
Yamashita A
Journal of the American Chemical Society, 107(20), 5823-5824 (1985)
G Carlie et al.
The British journal of dermatology, 149(4), 707-717 (2003-11-18)
Khellin is a naturally occurring furochromone which, when combined with artificial ultraviolet (UV) A or solar irradiation (KUVA), is reported to repigment vitiligo skin as effectively as PUVA photochemotherapy. The exact mechanism of KUVA-induced repigmentation is unknown. The aim of
Karin G Haug et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 45(1-2), 79-89 (2011-11-17)
Ammi visnaga L. (syn. Khella, Apiaceae) preparations have traditionally been used in the Middle East for the treatment of kidney stone disease. Visnagin, a furanocoumarin derivative, is one of the main compounds of Ammi visnaga with potential effects on kidney
Nishit S Patel et al.
Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.], 38(3), 381-391 (2012-02-01)
Vitiligo is an acquired multifocal and polygenic dyschromia that affects 1% to 3% of the world and presents as multiple depigmented macules and patches. Traditionally, the treatment of vitiligo has focused on pharmacologic interventions, but nearly half of all treated
Sally S El-Nakkady et al.
Acta poloniae pharmaceutica, 69(4), 645-655 (2012-08-11)
Bromination of visnaginone (1) yielded the dibromo derivative (2), which upon methylation with methyl iodide gave 1-(2,7-dibromo-4,6-dimethoxybenzofuran-5-yl) ethanone (3). Compound (3) reacted with dimethylformamide dimethylacetal to give (4). The reaction of (3) with aromatic aldehydes namely (vanillin, benzaldehyde and 3-anisaldehyde)
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