AFCDB: Dodecanoic acid (FDB003010)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:37 UTC

Update date

2020-09-17 15:38:38 UTC

Primary ID

FDB003010

Secondary Accession Numbers

FDB030978

Chemical Information

FooDB Name

Dodecanoic acid

Description

Dodecanoic acid also known as Lauric acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Lauric acid is a weakly acidic compound. It is a white, powdery solid with a faint odour of mild fatty coconut bay oil or soap. Dodecanoic acid is the main fatty acid in coconut oil (49%) and in palm kernel oil (47-50%), and is found in lesser amounts in wild nutmeg, human breast milk, cow‚Äôs milk, goat milk, watermelon seeds, plum and macadamia nut ( doi:10.1351/pac200173040685). Dodecanoic acid, although slightly irritating to mucous membranes, has an extremely low toxicity, is inexpensive, has antimicrobial properties and so is used in many soaps and shampoos. It is reacted with sodium hydroxide to generate sodium laurate, which is soap. Dodecanoic acid has been characterized as having "a more favorable effect on total HDL cholesterol than any other fatty acid either saturated or unsaturated" (PMID: 12716665).

CAS Number

143-07-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	5.13	ALOGPS
logP	4.48	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	58.68 m³·mol⁻¹	ChemAxon
Polarizability	25.85 Å³	ChemAxon
Number of Rings	0	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

C12H24O2

IUPAC name

dodecanoic acid

InChI Identifier

InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)

InChI Key

POULHZVOKOAJMA-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCC(O)=O

Average Molecular Weight

200.3178

Monoisotopic Molecular Weight

200.177630012

Classification

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:30805 )
straight-chain saturated fatty acid (CHEBI:30805 )
Straight chain fatty acids (C02679 )
Saturated fatty acids (C02679 )
Straight chain fatty acids (LMFA01010012 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Household products:

Antimicrobial agent:

Antibacterial

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 71.95%; H 12.08%; O 15.97%	DFC
Melting Point	Mp 44°	DFC
Boiling Point	Bp0.65 141-142° (lit. gives a pressure range)	DFC
Experimental Water Solubility	0.00481 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	4.60	SANGSTER (1993)
Experimental pKa	pKa 5.3 (20°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d20 0.88	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-074l-9100000000-911a01d38925d0de481f	2014-09-20	View Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-a12b321a54a44ae28972	Spectrum
GC-MS	Dodecanoic acid, 1 TMS, GC-MS Spectrum	splash10-014i-2910000000-d52410168e784872a5a6	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-06xx-9100000000-1ef5cd411f38c53a0a92	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0706-9100000000-e66a9147257053b93702	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0706-9100000000-2dd666a9a0355b1ca144	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-074i-9300000000-405ec308fe8c935c62a2	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-067i-0930000000-6a80d41e346f4b10104c	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-a12b321a54a44ae28972	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-2910000000-d52410168e784872a5a6	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-1910000000-8246864bf316bce609a2	Spectrum
Predicted GC-MS	Dodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9500000000-e05832f94ff0361363a2	Spectrum
Predicted GC-MS	Dodecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05g0-9310000000-038e232cccb44582ec9c	Spectrum
Predicted GC-MS	Dodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dodecanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-2290000000-861c4b7b2da35b82ef7f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4l-9100000000-966cf4c6621fcec41368	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-054o-9000000000-d43dd32656ad22e95fdd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-06xx-9100000000-a71409efaf5fdd6ab0e1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positive	splash10-0706-9100000000-eb09296a8c4c7c381b38	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-f22d8298d64e6f382279	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-0c79a7257b53685108c6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9600000000-25d268515337ef276c60	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-009b-9000000000-c00963f9b91f4a82e1ef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-f22d8298d64e6f382279	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-0c79a7257b53685108c6	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

3756

ChEMBL ID

Not Available

KEGG Compound ID

C02679

Pubchem Compound ID

3893

Pubchem Substance ID

Not Available

ChEBI ID

30805

Phenol-Explorer ID

Not Available

DrugBank ID

DB03017

HMDB ID

HMDB00638

CRC / DFC (Dictionary of Food Compounds) ID

CPX59-D:CPX59-D

EAFUS ID

1984

Dr. Duke ID

DODECANOIC-ACID|LAURIC-ACID

BIGG ID

40351

KNApSAcK ID

C00001221

HET ID

DAO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

143-07-7

GoodScent ID

rw1008181

SuperScent ID

Not Available

Wikipedia ID

Dodecanoic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Chebi: 18262

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 bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
candidicide			DUKE
cyclooxygenase-1 inhibitor	50630	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
hypercholesterolemic			DUKE

Enzymes

Name	Gene Name	UniProt ID
Peroxisomal carnitine O-octanoyltransferase	CROT	Q9UKG9
Carnitine O-palmitoyltransferase 2, mitochondrial	CPT2	P23786
Mitochondrial carnitine/acylcarnitine carrier protein	SLC25A20	O43772
S-acyl fatty acid synthase thioesterase, medium chain	OLAH	Q9NV23
Ganglioside GM2 activator	GM2A	P17900
Toll-like receptor 4	TLR4	O00206

Pathways

Name	SMPDB Link	KEGG Link
Beta Oxidation of Very Long Chain Fatty Acids	SMP00052	map01040
Fatty Acid Biosynthesis	SMP00456	Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids	SMP00481	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
metal	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
mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty	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.
bay oil	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

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Dodecanoic acid (FDB003010)

Structure for FDB003010 (Dodecanoic acid)