marmesin

Names

[ Name ]:
marmesin

[Synonym ]:
2-(2-Hydroxy-2-propanyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
(7S)-marmesin
marmesin
2-(2-hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-
2-(1-Hydroxy-1-methyl-ethyl)-2,3-dihydro-furo[3,2-g]chromen-7-one
S(+)-Marmesin
2-(1-Hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one
(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
S-(+)-Marmesin

Biological Activity

[Description]:

S-(+)-Marmesin is a natural coumarin, exhibiting COX-2/5-LOX dual inhibitory activity.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase

Research Areas >> Others

Natural Products >> Phenylpropanoids

[Target]

COX-2

5-Lipoxygenase

[In Vitro]

S-(+)-Marmesin ((+)-marmesin) shows affinity at the recombinant psoralen synthase, with a Km of 1.5 ± 0.5 μM, exceeding the substrate affinities of other enzymes of the CYP71 subfamily involved in plant secondary metabolism[1]. S-(+)-Marmesin ((+)-marmesin) shows COX-2/5-LOX dual inhibitory activity[2].

[References]

[1]. Larbat R, et al. Molecular cloning and functional characterization of psoralen synthase, the first committed monooxygenase of furanocoumarin biosynthesis. J Biol Chem. 2007 Jan 5;282(1):542-54. Epub 2006 Oct 26.

[2]. Kim JS, et al. Chemical constituents of the root of Dystaenia takeshimana and their anti-inflammatory activity. Arch Pharm Res. 2006 Aug;29(8):617-23.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
434.0±45.0 °C at 760 mmHg

[ Melting Point ]:
189-191℃

[ Molecular Formula ]:
C₁₄H₁₄O₄

[ Molecular Weight ]:
246.259

[ Flash Point ]:
168.0±22.2 °C

[ Exact Mass ]:
246.089203

[ PSA ]:
59.67000

[ LogP ]:
1.69

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.611

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LV1045500

CHEMICAL NAME :: 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-

CAS REGISTRY NUMBER :: 13849-08-6

LAST UPDATED :: 199410

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C14-H14-O4

MOLECULAR WEIGHT :: 246.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 1040 ng/plate

REFERENCE :: JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub., 1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76- Volume(issue)/page/year: 13,521,1984