Milk Composition Database: Showing metabocard for Palmitic acid (BMDB0000220)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:56 UTC

Update Date

2020-06-04 22:58:27 UTC

MCDB ID

BMDB0000220

Secondary Accession Numbers

BMDB00220

Metabolite Identification

Common Name

Palmitic acid

Description

Palmitic acid, also known as C16 or palmitate, 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. Palmitic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Palmitic acid exists in all living species, ranging from bacteria to humans. Palmitic acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Hexyldecanoic acid	ChEBI
1-Pentadecanecarboxylic acid	ChEBI
16:00	ChEBI
C16	ChEBI
C16 Fatty acid	ChEBI
C16:0	ChEBI
Cetylic acid	ChEBI
CH3-[CH2]14-COOH	ChEBI
FA 16:0	ChEBI
Hexadecanoate	ChEBI
Hexadecoic acid	ChEBI
Hexadecylic acid	ChEBI
Hexaectylic acid	ChEBI
N-Hexadecanoic acid	ChEBI
N-Hexadecoic acid	ChEBI
Palmitate	ChEBI
Palmitinic acid	ChEBI
Palmitinsaeure	ChEBI
Pentadecanecarboxylic acid	ChEBI
1-Hexyldecanoate	Generator
1-Pentadecanecarboxylate	Generator
Cetylate	Generator
Hexadecanoic acid	Generator
Hexadecoate	Generator
Hexadecylate	Generator
Hexaectylate	Generator
N-Hexadecanoate	Generator
N-Hexadecoate	Generator
Palmitinate	Generator
Pentadecanecarboxylate	Generator
Edenor C16	HMDB
Emersol 140	HMDB
Emersol 143	HMDB
Glycon p-45	HMDB
Hexadecanoate (N-C16:0)	HMDB
Hexadecanoic acid palmitic acid	HMDB
Hydrofol	HMDB
Hydrofol acid 1690	HMDB
Hystrene 8016	HMDB
Hystrene 9016	HMDB
Industrene 4516	HMDB
Kortacid 1698	HMDB
Loxiol ep 278	HMDB
Lunac p 95	HMDB
Lunac p 95KC	HMDB
Lunac p 98	HMDB
Palmitoate	HMDB
Palmitoic acid	HMDB
PAM	HMDB
PLM	HMDB
Prifac 2960	HMDB
Prifrac 2960	HMDB
Pristerene 4934	HMDB
Univol u332	HMDB
Acid, hexadecanoic	HMDB
Acid, palmitic	HMDB
FA(16:0)	HMDB

Chemical Formula

C₁₆H₃₂O₂

Average Molecular Weight

256.4241

Monoisotopic Molecular Weight

256.240230268

IUPAC Name

hexadecanoic acid

Traditional Name

palmitic acid

CAS Registry Number

57-10-3

SMILES

CCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

InChI Key

IPCSVZSSVZVIGE-UHFFFAOYSA-N

Chemical Taxonomy

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:15756 )
straight-chain saturated fatty acid (CHEBI:15756 )
Straight chain fatty acids (C00249 )
Saturated fatty acids (C00249 )
Straight chain fatty acids (LMFA01010001 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	61.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.0e-05 mg/mL	Not Available
LogP	7.17	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	7.23	ALOGPS
logP	6.26	ChemAxon
logS	-5.8	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	14	ChemAxon
Refractivity	77.08 m³·mol⁻¹	ChemAxon
Polarizability	34.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-014i-0901000000-51ee83f9462d25fa4045	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0100-9700000000-3d8b6cf4736afa482b57	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2901000000-fb423e89a78708021db1	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0abc-9110000000-6d7f0dbe5b588850b941	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0901000000-51ee83f9462d25fa4045	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0100-9700000000-3d8b6cf4736afa482b57	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2901000000-fb423e89a78708021db1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2901000000-fb423e89a78708021db1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1900000000-d7638a578d846871e670	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9610000000-f75185fa40c090817f46	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-022i-9440000000-7d3a81432d58729f9f98	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-0090000000-39c3a0e17432781e9760	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0090000000-8ec1a6953701fc22ce27	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0fba-9200000000-23c995bf81d5ef609489	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0abc-9110000000-12f1884d67998fb924a5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0091000000-4f6858c1cc0f04cbabf5	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0090000000-14e58eecd83ba52123c2	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0090000000-c3f9f4d5c336137b7fcf	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0090000000-47919da3faa8e0f52bbc	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0090000000-fdd9e98416da12470fe9	2017-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06xx-9100000000-7ac9cd088cb9cb9f7560	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	45628 +/- 15209 uM	Total fatty acid	PMID: 16899705	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected and Quantified	48864 +/- 11699 uM	Total fatty acid	M. Ferrand et al....	details
Detected and Quantified	49098 +/- 11270 uM	Total fatty acid	M. Ferrand et al....	details
Detected but not Quantified	Not Applicable		PMID: 1779072	details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected and Quantified	16691 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	15989 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	3470 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	5304 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	3470 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	40167 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	38998 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	36659 uM	Total fatty acid	Fooddata+, T...	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected and Quantified	396609 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	458615 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	479284 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	491373 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	90.04 +/- 12.70 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	106.07 +/- 14.43 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	50.79 +/- 2.60 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	13.85 +/- 2.31 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	78.82 +/- 1.33 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	124 +/- 1 uM	Free fatty acid	Catrienus De Jong...	details
Detected and Quantified	220.8 +/- 41.8 uM	Free fatty acid	PMID: 11754544	details
Detected and Quantified	131.1 +/- 22.8 uM	Free fatty acid	PMID: 11754544	details
Detected and Quantified	29 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	104 +/- 4 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	54.3 +/- 2.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	47.3 +/- 2.3 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000220

DrugBank ID

DB03796

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15756

References

Synthesis Reference

Xu, Yan; Ling, Li. A method for preparing conjugated linoleic acid and palmitic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11. [PubMed:9718493 ]
Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Palmitic acid (BMDB0000220)

Structure for BMDB0000220 (Palmitic acid)