Showing Compound Rotundifolone (FDB016026)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:11 UTC

Update date

2019-11-26 03:12:38 UTC

Primary ID

FDB016026

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Rotundifolone

Description

Rotundifolone belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Rotundifolone is a herbal and minty tasting compound. Rotundifolone is found, on average, in the highest concentration within spearmints (Mentha spicata) and cornmints (Mentha arvensis). Rotundifolone has also been detected, but not quantified in, herbs and spices. This could make rotundifolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Rotundifolone.

CAS Number

5945-46-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Epoxy-P-menth-4(8)-en-3-one	HMDB
2,3-Epoxy-6-isopropylidene-3-methylcyclohexanone	HMDB
6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9ci	HMDB
Piperitenone oxide	HMDB
6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9CI	db_source
P-Menth-4(8)-en-3-one, 1,2-epoxy-	biospider
Rotundifolone	db_source

Predicted Properties

Property	Value	Source
Water Solubility	8.95 g/L	ALOGPS
logP	1.61	ALOGPS
logP	2.07	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.56 m³·mol⁻¹	ChemAxon
Polarizability	18.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H14O2

IUPAC name

6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one

InChI Identifier

InChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3

InChI Key

AKASWINDKIEEBO-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=C1CCC2(C)OC2C1=O

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

Classification

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 72.26%; H 8.49%; O 19.25%	DFC
Melting Point	Mp 27.5°	DFC
Boiling Point	Bp1 86°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]10D +166.5 (MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Rotundifolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00o4-9300000000-28ac35eefccb97ecf8f7	Spectrum
Predicted GC-MS	Rotundifolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-0d2244bb050ca70a3c49	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-4900000000-a49b13c97830692f36f0	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-067i-9100000000-5d3ca3ad1a2c8d254117	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-ab194c3e028cf03581b8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-a1934865dd6aa8ca0d4a	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9600000000-37561a809cd7b097631e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-d1252c53df5aa0366a66	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9300000000-442ba93afe2056decf39	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1900000000-d8e5853d91f1eb90687c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9300000000-0dfe3b6fd9baf52e4fd7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9100000000-6c52be035dfdc4e36ed2	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

55800

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

61942

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB37044

CRC / DFC (Dictionary of Food Compounds) ID

KMC41-G:KMC41-G

EAFUS ID

3056

Dr. Duke ID

PIPERITENONE-OXIDE|(+)-PIPERITENONE-OXIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1049431

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti acetylcholinesterase	38462	An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure.	DUKE
Insecticide	24852	An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).