Showing Compound Carnaubic acid (FDB004651)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:20 UTC

Update date

2019-11-26 03:00:09 UTC

Primary ID

FDB004651

Secondary Accession Numbers

FDB021823

Chemical Information

FooDB Name

Carnaubic acid

Description

Lignoceric acid, also known as N-tetracosanoic acid or tetraeicosanoate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, lignoceric acid is considered to be a fatty acid lipid molecule. Lignoceric acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lignoceric acid can be found in a number of food items such as hazelnut, cheese, rye bread, and cetacea (dolphin, porpoise, whale), which makes lignoceric acid a potential biomarker for the consumption of these food products. Lignoceric acid can be found primarily in blood and feces, as well as in human fibroblasts tissue. Lignoceric acid exists in all eukaryotes, ranging from yeast to humans. In humans, lignoceric acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Lignoceric acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid (1.1% – 2.2%). This fatty acid is also a byproduct of lignin production .

CAS Number

557-59-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
CH3-[CH2]22-COOH	ChEBI
Lignoceric acid	ChEBI
Lignozerinsaeure	ChEBI
N-Tetracosanoic acid	ChEBI
Tetracosanic acid	ChEBI
Tetracosansaeure	ChEBI
Tetracosoic acid	ChEBI
Tetraeicosanoic acid	ChEBI
Tetraicosanoic acid	ChEBI
Lignocerate	Generator
N-Tetracosanoate	Generator
Tetracosanate	Generator
Tetracosoate	Generator
Tetraeicosanoate	Generator
Tetraicosanoate	Generator
Tetracosanoate	Generator
Lignoceric acid, silver (1+) salt	HMDB
Lignoceric acid, sodium salt	HMDB
Lignoceric acid, potassium salt	HMDB
Tetracosanoic acid, potassium salt (1:1)	HMDB
Potassium tetracosanoate	HMDB
Tetracosanoic acid	MeSH
FA(24:0)	PhytoBank

Predicted Properties

Property	Value	Source
Water Solubility	2.3e-05 g/L	ALOGPS
logP	9.56	ALOGPS
logP	9.81	ChemAxon
logS	-7.2	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	22	ChemAxon
Refractivity	113.89 m³·mol⁻¹	ChemAxon
Polarizability	51.57 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

C24H48O2

IUPAC name

tetracosanoic acid

InChI Identifier

InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)

InChI Key

QZZGJDVWLFXDLK-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

368.6367

Monoisotopic Molecular Weight

368.36543078

Classification

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very 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

very long-chain fatty acid (CHEBI:28866 )
straight-chain saturated fatty acid (CHEBI:28866 )
Straight chain fatty acids (C08320 )
Saturated fatty acids (C08320 )
Straight chain fatty acids (LMFA01010024 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Cell:

Fibroblast

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0avl-9200000000-6a6f857b59886189b246	2014-09-20	View Spectrum
GC-MS	Carnaubic acid, non-derivatized, GC-MS Spectrum	splash10-0159-1900000000-3507c183bf018486d18f	Spectrum
GC-MS	Carnaubic acid, 1 TMS, GC-MS Spectrum	splash10-0159-2900000000-9dedfb3583ae4e553948	Spectrum
GC-MS	Carnaubic acid, non-derivatized, GC-MS Spectrum	splash10-07bf-9000000000-2ae141518702212751a7	Spectrum
GC-MS	Carnaubic acid, non-derivatized, GC-MS Spectrum	splash10-0159-1900000000-3507c183bf018486d18f	Spectrum
GC-MS	Carnaubic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2900000000-9dedfb3583ae4e553948	Spectrum
GC-MS	Carnaubic acid, non-derivatized, GC-MS Spectrum	splash10-0159-1900000000-2826f8c66ba3647dda0f	Spectrum
Predicted GC-MS	Carnaubic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-7690000000-51ad38c3eba8f98c3565	Spectrum
Predicted GC-MS	Carnaubic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00g0-9550000000-6d38b4af18d7872e12a9	Spectrum
Predicted GC-MS	Carnaubic acid, non-derivatized, 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)	splash10-016r-0509000000-b590f3868a4aa3c86803	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0903000000-a6d1b482b61c2d36ee1d	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-0900000000-4ef3dd8c92115a6d4e0c	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-07bf-9000000000-2ae141518702212751a7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0900000000-3c3e69329be8a7148076	2012-08-31	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 10V, Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0009000000-5c9df57aa4e8e48bd80f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-a22a23dbfe780a163a38	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-7907c6ab3ef19e9cdf86	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0009000000-847587fdc96a653e9651	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0009000000-5c9df57aa4e8e48bd80f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0009000000-a22a23dbfe780a163a38	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0009000000-847587fdc96a653e9651	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-3c3e69329be8a7148076	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0009000000-847587fdc96a653e9651	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0009000000-7bccb707d42bca681a58	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-a22a23dbfe780a163a38	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-48bd2e6f8cbaa8fda6bd	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-2339000000-6881995e14be93cee803	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-6982000000-bcce0a5d41ac456500c7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-249bc2a1e0da9132abb1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-0009000000-bb2e8d3e4fc1a5f88c77	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9113000000-18bb969031b0d8959a2f	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

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

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CARNAUBIC-ACID

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

Not Available

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).

Showing Compound Carnaubic acid (FDB004651)

Structure for FDB004651 (Carnaubic acid)