AFCDB: Octadecanoic acid (FDB002941)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:35 UTC

Update date

2020-09-17 15:42:17 UTC

Primary ID

FDB002941

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Octadecanoic acid

Description

Stearic acid, also known as stearate or octadecanoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a waxy solid and is one of the most common saturated fatty acids found in nature (being a close second to palmitic acid). The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is obtained from fats and oils by the saponification of the triglycerides, like stearin, using hot water. Stearic acid exists in all living organisms, ranging from bacteria to humans. Stearic acid has been detected, but not quantified in, several different foods, such as sweet bay, rose hips, muscadine grapes, pummelo, and garland chrysanthemums. Fats and oils rich in stearic acid are more abundant in animal fat (up to 30%) than in vegetable fat (typically <5%). The important exceptions are the foods cocoa butter and shea butter, where the stearic acid content (as a triglyceride) is 28‚Äì45%. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks. Stearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products. Fatty acids are classic components of candle-making. Stearic acid is used along with simple sugar or corn syrup as a hardener in candies. In epidemiologic and clinical studies, stearic acid was found to be associated with lowered LDL cholesterol in comparison with other saturated fatty acids (PMID:19939984).

CAS Number

57-11-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.6e-05 g/L	ALOGPS
logP	8.02	ALOGPS
logP	7.15	ChemAxon
logS	-6.6	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	16	ChemAxon
Refractivity	86.29 m³·mol⁻¹	ChemAxon
Polarizability	38.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H36O2

IUPAC name

octadecanoic acid

InChI Identifier

InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)

InChI Key

QIQXTHQIDYTFRH-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

284.4772

Monoisotopic Molecular Weight

284.271530396

Classification

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-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

long-chain fatty acid (CHEBI:28842 )
saturated fatty acid (CHEBI:28842 )
straight-chain saturated fatty acid (CHEBI:28842 )
Straight chain fatty acids (C01530 )
Saturated fatty acids (C01530 )
Straight chain fatty acids (LMFA01010018 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 76.00%; H 12.75%; O 11.25%	DFC
Melting Point	Mp 69.7°	DFC
Boiling Point	Bp5 213°	DFC
Experimental Water Solubility	0.000597 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	8.23	SANGSTER (1993)
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0c03-9200000000-5dd52f837d56d80fa968	2014-09-20	View Spectrum
GC-MS	Octadecanoic acid, 1 TMS, GC-MS Spectrum	splash10-0159-1900000000-9cc966384906cd35537d	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0900000000-b87a9955374d11966ba6	Spectrum
GC-MS	Octadecanoic acid, 1 TMS, GC-MS Spectrum	splash10-0100-9700000000-979da356343fa0697993	Spectrum
GC-MS	Octadecanoic acid, 1 TMS, GC-MS Spectrum	splash10-0159-2901000000-16194c704b7abd193647	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-06yo-9110000000-6f345827577cdc861aca	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-075c-9220000000-207b53a511763954eb66	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-1900000000-9cc966384906cd35537d	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0900000000-b87a9955374d11966ba6	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0100-9700000000-979da356343fa0697993	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2901000000-16194c704b7abd193647	Spectrum
GC-MS	Octadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-1900000000-d34fc01a79cc27a32080	Spectrum
Predicted GC-MS	Octadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9540000000-c6c002443ac3a40dabdb	Spectrum
Predicted GC-MS	Octadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-009l-9551000000-b9a196da32e6273fad4f	Spectrum
Predicted GC-MS	Octadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Octadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Octadecanoic 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, Negative (Annotated)	splash10-001i-0090000000-1368043827a20e28c172	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001i-0090000000-5c3fa1d38cf3d0a38d74	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-9441e6362046ae198384	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-f629b105972a0728beb6	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-fbf3f8e91badb0ec251d	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00lr-0090000000-a702a9f469dbb513856a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-9441e6362046ae198384	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-fbf3f8e91badb0ec251d	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-34a309d09cb2def46a19	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4690000000-f68e827f7ebccd80d5bf	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8920000000-2e865f09d760af582c07	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-34a309d09cb2def46a19	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4690000000-f68e827f7ebccd80d5bf	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8920000000-2e865f09d760af582c07	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-b3ce35f839a30b41c718	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-1b84b49819fa37fce1ae	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-b3ce35f839a30b41c718	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-1b84b49819fa37fce1ae	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
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28842

Phenol-Explorer ID

Not Available

DrugBank ID

DB03193

HMDB ID

HMDB00827

CRC / DFC (Dictionary of Food Compounds) ID

CPL65-U:CPL65-U

EAFUS ID

3541

Dr. Duke ID

OCTADECANOIC-ACID|STEARIC-ACID

BIGG ID

37799

KNApSAcK ID

C00032087

HET ID

STE

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1009271

SuperScent ID

Not Available

Wikipedia ID

Stearic acid

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
5alpha-reductase inhibitor	50781	An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.	DUKE
cosmetic	64857	The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
hypocholesterolemic			DUKE
lubricant			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
propecic			DUKE
suppository			DUKE

Enzymes

Name	Gene Name	UniProt ID
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Liver carboxylesterase 1	CES1	P23141
Pancreatic triacylglycerol lipase	PNLIP	P16233
Hepatic triacylglycerol lipase	LIPC	P11150
Inactive pancreatic lipase-related protein 1	PNLIPRP1	P54315
Patatin-like phospholipase domain-containing protein 3	PNPLA3	Q9NST1
Gastric triacylglycerol lipase	LIPF	P07098
Endothelial lipase	LIPG	Q9Y5X9
Pancreatic lipase-related protein 2	PNLIPRP2	P54317
Lipoprotein lipase	LPL	P06858
Patatin-like phospholipase domain-containing protein 4	PNPLA4	P41247
Patatin-like phospholipase domain-containing protein 2	PNPLA2	Q96AD5
Pancreatic lipase-related protein 3	PNLIPRP3	Q17RR3
Cholinesterase	BCHE	P06276
Carboxylesterase 5A	CES5A	Q6NT32
60 kDa lysophospholipase	ASPG	Q86U10
Fatty acid synthase	FASN	P49327
Galactoside-binding soluble lectin 13	LGALS13	Q9UHV8
Eosinophil lysophospholipase	CLC	Q05315
Cocaine esterase	CES2	O00748
Acylphosphatase-2	ACYP2	P14621
Acylphosphatase-1	ACYP1	P07311
Aspartoacylase	ASPA	P45381
Aspartoacylase-2	ACY3	Q96HD9
Acid ceramidase	ASAH1	Q13510
Homeodomain-interacting protein kinase 1	HIPK1	Q86Z02
Peroxisome proliferator-activated receptor gamma	PPARG	P37231
Long-chain fatty acid transport protein 6	SLC27A6	Q9Y2P4
Long-chain fatty acid transport protein 3	SLC27A3	Q5K4L6
Long-chain fatty acid transport protein 4	SLC27A4	Q6P1M0
Putative neutral ceramidase C	ASAH2C	P0C7U2
Alkaline ceramidase 2	ACER2	Q5QJU3
Neutral ceramidase	ASAH2	Q9NR71
Alkaline ceramidase 1	ACER1	Q8TDN7
Neuropathy target esterase	PNPLA6	Q8IY17
Carboxylesterase 3	CES3	Q6UWW8
S-acyl fatty acid synthase thioesterase, medium chain	OLAH	Q9NV23
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2

Pathways

Name	SMPDB Link	KEGG Link
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids	SMP00482	Not Available
Plasmalogen Synthesis	SMP00479	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Files

MSDS

show

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.

Octadecanoic acid (FDB002941)

Structure for FDB002941 (Octadecanoic acid)