ChemFOnt: Showing chemical card for delta-Hexanolactone (CFc000000347)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:43 UTC

Chemfont ID

CFc000000347

Molecule Identification

Common Name

delta-Hexanolactone

Definition

delta-Hexanolactone is the lactone of 5-hydroxyhexanoic acid. Lactones are internal esters that exist in equilibrium between their closed (lactone) and open (hydroxy acid) forms in an aqueous environment. The lactone/hydroxy acid ratio at equilibrium is pH-dependent, with the closed form being favored at lower pH values, and can be greatly influenced by structural features of the lactone such as the ring size, substituents on the ring and the presence of double bonds within the ring. Many drugs and endogenous compounds are lactones or hydroxy acids and an enzyme capable of catalyzing the interchange between the open and closed forms in vivo could have pronounced effects upon their biological activity and/or distribution. delta-Hexanolactone is the substrate of paraoxonases (PON) in humans. Human PON1 hydrolyzes over 30 different lactones (cyclic esters) and catalyzes the reverse reaction (lactonization) of a broad range of hydroxy acids. Hydroxy acid lactonization or lactone hydrolysis is catalyzed until equilibrium between the open and closed forms is reached (PMID: 15772423 , 12963475 , 12963475 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Δ-hexanolactone	Generator
Epsilon-Caprolactone	HMDB
(RS)-delta-Hexalactone	HMDB
5-Hexanolide	HMDB
5-Hydroxy-hexanoate	HMDB
5-Hydroxy-hexanoic acid	HMDB
5-Hydroxy-hexanoic acid lactone	HMDB
5-Hydroxyhexanoate	HMDB
5-Hydroxyhexanoic acid	HMDB
5-Hydroxyhexanoic acid lactone	HMDB
6-Methyl-D-valerolactone	HMDB
6-Methylvalerolactone	HMDB
delta-Caprolactone	HMDB
delta-Hexalactone	HMDB
delta-Hexanolide	HMDB
delta-Methyl-delta-valerolactone	HMDB
Hexanolactone	HMDB
Tetrahydro-6-methyl-2H-pyran-2-one	HMDB

Chemical Formula

C₆H₁₀O₂

Average Molecular Weight

114.1424

Monoisotopic Molecular Weight

114.068079564

IUPAC Name

6-methyloxan-2-one

Traditional Name

hexanolactone

CAS Registry Number

823-22-3

SMILES

CC1CCCC(=O)O1

InChI Identifier

InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3

InChI Key

RZTOWFMDBDPERY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta_valerolactone
Delta valerolactone
Oxane
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Herbal

Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0000453)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000453)

Source

Endogenous

Endogenous (HMDB: HMDB0000453)

Plant

Plant (HMDB: HMDB0000453)

Animal

Animal (HMDB: HMDB0000453)

Exogenous

Food

Food (HMDB: HMDB0000453)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Fruit

Fruits (FooDB: FOOD00871)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	24.1 g/L	ALOGPS
logP	0.93	ALOGPS
logP	1.01	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	29.33 m³·mol⁻¹	ChemAxon
Polarizability	12.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon