ChemFOnt: Showing chemical card for 8-Hydroxy-6-methoxy-3-methyl-3,4-dihydroisocoumarin (CFc000334978)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:27:14 UTC

Chemfont ID

CFc000334978

Molecule Identification

Common Name

8-Hydroxy-6-methoxy-3-methyl-3,4-dihydroisocoumarin

Definition

6-methoxymellein, also known as 6-mhmd-isocoumarin, is a member of the class of compounds known as 2-benzopyrans. 2-benzopyrans are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. 6-methoxymellein is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 6-methoxymellein can be found in carrot, root vegetables, and wild carrot, which makes 6-methoxymellein a potential biomarker for the consumption of these food products. 6-methoxymellein is a dihydroisocoumarin, a phenolic compound found in carrots and carrot purées. It is responsible for bitterness in carrots. It is a phytoalexin, induced in carrot slices by UV-C, that allows resistance to Botrytis cinerea and other microorganisms .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,4-Dihydro-8-hydroxy-6-methoxy-3-methyl-1H-2-benzopyran-1-one	ChEBI
3,4-Dihydro-8-hydroxy-6-methoxy-3-methylisocoumarin	ChEBI
3-Methyl-6-methoxy-8-hydroxy-3,4-dihydroisocoumarin	ChEBI
6-Methoxy-8-hydroxy-3-methyl-3,4-dihydroisocoumarin	ChEBI
6-MHMD-Isocoumarin	ChEBI
3,4-dihydro-8-Hydroxy-6-methoxy-3-methyl-1H-2-benzopyran-1-one	HMDB
Antibiotic LL-N313a	HMDB
Isocoumarin	HMDB
LL-N313a	HMDB
6-Methoxy-8-hydroxy-3-methyl-3,4-dihydroisocoumarin, (R)-(-)-isomer	MeSH, HMDB

Chemical Formula

C₁₁H₁₂O₄

Average Molecular Weight

208.2106

Monoisotopic Molecular Weight

208.073558872

IUPAC Name

8-hydroxy-6-methoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

6-methoxymellein

CAS Registry Number

13410-15-6

SMILES

COC1=CC(O)=C2C(=O)OC(C)CC2=C1

InChI Identifier

InChI=1S/C11H12O4/c1-6-3-7-4-8(14-2)5-9(12)10(7)11(13)15-6/h4-6,12H,3H2,1-2H3

InChI Key

AIFNAMVERSBWPS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isochromanes (CHEBI:16252 )
a small molecule (6-METHOXYMELLEIN )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0038510)

Food

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.97 g/L	ALOGPS
logP	2.06	ALOGPS
logP	2.42	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	54.26 m³·mol⁻¹	ChemAxon
Polarizability	21.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon