Showing Compound 5-Dodecanolide (FDB016873)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:42 UTC

Update date

2019-11-26 03:13:53 UTC

Primary ID

FDB016873

Secondary Accession Numbers

FDB017639
FDB016874

Chemical Information

FooDB Name

5-Dodecanolide

Description

Xi-5-dodecanolide, also known as (+/-)-6-heptyltetrahydro-2h-pyran-2-one or (+/-)-delta-heptyl-delta-valerolactone, is a member of the class of compounds known as delta valerolactones. Delta valerolactones are cyclic organic compounds containing an oxan-2- one moiety. Thus, xi-5-dodecanolide is considered to be a fatty ester lipid molecule. Xi-5-dodecanolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Xi-5-dodecanolide can be found in alcoholic beverages, fruits, herbs and spices, and milk and milk products, which makes xi-5-dodecanolide a potential biomarker for the consumption of these food products.

CAS Number

3051-22-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(+/-)-5-dodecanolide	HMDB
(+/-)-6-heptyltetrahydro-2H-pyran-2-one	HMDB
(+/-)-delta-heptyl-delta-valerolactone	HMDB
5-Dodecalactone	HMDB
5-Hydroxydodecanoic acid delta-lactone	HMDB
5-Hydroxydodecanoic acid lactone	HMDB
6-heptyltetrahydro-2H-Pyran-2-one	HMDB
delta-Dodecalactone	HMDB
delta-Dodecanolactone	HMDB
delta-Heptyl-delta-valerolactone	HMDB
Dodecan-5-olide	HMDB
Dodecanoic acid, 5-hydroxy-, delta-lactone	HMDB
Dodecanolide-1,5	HMDB
N-Heptyl-delta-valerolactone	HMDB
Δ-dodecalactone	Generator
5-Dodecanolide	db_source
d-Dodecalactone	db_source
FEMA 2401	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	4.34	ALOGPS
logP	3.76	ChemAxon
logS	-4	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	6	ChemAxon
Refractivity	56.86 m³·mol⁻¹	ChemAxon
Polarizability	24.59 Å³	ChemAxon
Number of Rings	1	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

C12H22O2

IUPAC name

6-heptyloxan-2-one

InChI Identifier

InChI=1S/C12H22O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h11H,2-10H2,1H3

InChI Key

QRPLZGZHJABGRS-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCC1CCCC(=O)O1

Average Molecular Weight

198.3019

Monoisotopic Molecular Weight

198.161979948

Classification

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

Lactones (LMFA07040040 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 72.68%; H 11.18%; O 16.14%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	5-Dodecanolide, non-derivatized, GC-MS Spectrum	splash10-006y-9000000000-6dde1f4e9eb6e77e2909	Spectrum
GC-MS	5-Dodecanolide, non-derivatized, GC-MS Spectrum	splash10-006y-9000000000-6dde1f4e9eb6e77e2909	Spectrum
Predicted GC-MS	5-Dodecanolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gv-9300000000-81e2985e9c436226c577	Spectrum
Predicted GC-MS	5-Dodecanolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Dodecanolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03e9-0900000000-4a1c0c068526fdf84a51	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03ka-3900000000-85aa811e6aabe9eb2fab	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0900000000-edf9460e6f07bc10701b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0900000000-4a1c0c068526fdf84a51	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03ka-3900000000-85aa811e6aabe9eb2fab	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-5faedf2b3da12ffb907d	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08fr-3900000000-30ec084bc09f83f3e01a	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9200000000-19972997d12efa7d2d2f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0900000000-19f313ff46494d79b1ce	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-3900000000-dc38a126e161e45a8bb0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-7265f487c6f2a2594411	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4j-9300000000-09c5d1f0cecc8213d189	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9100000000-136b583c75cfd1b47a70	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-abfe093fcccf0157ec26	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-e1c4c7edfac216993e06	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-3900000000-ad70e93c53aebe76e52a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-6900000000-eba8dee2f97ccb9a51ba	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

KTS02-U:KTS02-U

EAFUS ID

1073

Dr. Duke ID

DELTA-DODECALACTONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

713-95-1

GoodScent ID

rw1013351

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
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
fruit	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
metallic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peach	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
buttery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.