ContaminantDB: Hexacosanoic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:15:25 UTC

Update Date

2026-04-17 17:22:27 UTC

Accession Number

CHEM003246

Identification

Common Name

Hexacosanoic acid

Class

Small Molecule

Description

Hexacosanoic acid, or cerotic acid, is a 26-carbon long-chain saturated fatty acid with the chemical formula CH3(CH2)24COOH. It is most commonly found in beeswax and carnauba wax, and is a white crystalline solid. (Wikipedia) X-linked adrenoleukodystrophy (X-ALD) is a peroxisomal disorder biochemically characterized by the accumulation of very long chain fatty acids (VLCFA), particularly hexacosanoic acid (C(26:0)) and tetracosanoic acid (C(24:0)), in tissues and biological fluids. (1)

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C26:0	ChEBI
Ceratinic acid	ChEBI
Ceric acid	ChEBI
Cerinic acid	ChEBI
Cerotic acid	ChEBI
Cerotinic acid	ChEBI
Cerylic acid	ChEBI
CH3-[CH2]24-COOH	ChEBI
Hexacosansaeure	ChEBI
Hexacosoic acid	ChEBI
Hexaeicosanoic acid	ChEBI
N-C26:0	ChEBI
N-Hexacosanoic acid	ChEBI
Ceratinate	Generator
Cerate	Generator
Cerinate	Generator
Cerotate	Generator
Cerotinate	Generator
Cerylate	Generator
Hexacosoate	Generator
Hexaeicosanoate	Generator
N-Hexacosanoate	Generator
Hexacosanoate	Generator
Hexacosanoate (N-C26:0)	HMDB
Hexacosanoic acid	PhytoBank
FA(26:0)	PhytoBank

Chemical Formula

C₂₆H₅₂O₂

Average Molecular Mass

396.690 g/mol

Monoisotopic Mass

396.397 g/mol

CAS Registry Number

506-46-7

IUPAC Name

hexacosanoic acid

Traditional Name

hexacosanoic acid

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C26H52O2/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(27)28/h2-25H2,1H3,(H,27,28)

InChI Key

XMHIUKTWLZUKEX-UHFFFAOYSA-N

Chemical Taxonomy

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:31009 )
straight-chain saturated fatty acid (CHEBI:31009 )
Straight chain fatty acids (LMFA01010026 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Adrenal Gland
Fibroblasts

Pathways

Name	SMPDB Link	KEGG Link
Beta Oxidation of Very Long Chain Fatty Acids	SMP00052	map01040
Adrenoleukodystrophy, X-linked	SMP00516	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystalline solid.

Experimental Properties

Property	Value
Melting Point	88.5°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.8e-05 g/L	ALOGPS
logP	9.87	ALOGPS
logP	10.7	ChemAxon
logS	-7.3	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	24	ChemAxon
Refractivity	123.09 m³·mol⁻¹	ChemAxon
Polarizability	55.83 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	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2900100000-dc0324482e5853e76290	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2900100000-dc0324482e5853e76290	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2900100000-dc0324482e5853e76290	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1900000000-9d83fa08f63878dd9794	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8890000000-a358b076f9e4d3b08976	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fmr-9550000000-f90d4cc6a83ff8e16245	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4j-0109000000-bc2c74027165503fd92f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0pb9-2193000000-cf0ac4a96f99022c7b3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0w30-6096000000-65025824de97c5fb5ff7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-00lr-0009000000-998e2947790abd467bc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0009000000-bd3c909a0431684b20e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ug1-3439000000-ca5336c838aa14069626	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-6974000000-93ebd8f603ed3f48dd9d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-50e9c7751bdac41b78c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0009000000-fdc9aa019c323235312e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9113000000-af814ec2317a697df1a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-87ff11014d638fb7aedd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-1009000000-28b98f74e9fa6d052c38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9003000000-9b4d6e9900769e9411a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2009000000-459e9bac675c0081de3d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-7039000000-16142145274003e6395d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9010000000-33f6f730f4cbdee5a975	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0597-9201000000-41113a5b904c5db7332d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Ingestion

Mechanism of Toxicity

Adrenoleukodystrophy (ALD) is caused by mutations in ABCD1, a gene located on the X chromosome that codes for ALD, a peroxisomal membrane transporter protein. The exact mechanism of the pathogenesis of the various forms of ALD is not known. Biochemically, individuals with ALD show very high levels of unbranched, saturated, very long chain fatty acids, particularly cerotic acid (26:0). The level of cerotic acid in plasma does not correlate with clinical presentation. (Wikipedia)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Hexacosanoic acid is most commonly found in beeswax and carnauba wax (Wikipedia). It is also an endogenously produced metabolite found in the human body.

Minimum Risk Level

Not Available

Health Effects

Hexacosanoic acid, or cerotic acid, is associated with adrenoleukodystrophy (also known as X-linked adrenoleukodystrophy, ALD, X-ALD, adrenomyeloneuropathy, AMN, Siemerling–Creutzfeldt disease or bronze Schilder disease) is a disorder of peroxisomal fatty acid beta oxidation which results in the accumulation of very-long chain fatty acids in tissues throughout the body. The most severely affected tissues are the myelin in the central nervous system, the adrenal cortex and the Leydig cells in the testes. (Wikipedia)

Symptoms

Clinically, adrenoleukodystrophy (ALD) is a heterogenous disorder, presenting with several distinct phenotypes, and no clear pattern of genotype-phenotype correlation. As an X-linked disorder, ALD presents most commonly in males, however approximately 50% of heterozygote females show some symptoms later in life. Approximately two-thirds of ALD patients will present with the childhood cerebral form of the disease, which is the most severe form. It is characterized by normal development in early childhood, followed by rapid degeneration to a vegetative state. The other forms of ALD vary in terms of onset and clinical severity, ranging from adrenal insufficiency to progressive paraparesis in early adulthood (this form of the disease is typically known as adrenomyeloneuropathy). (Wikipedia)

Treatment

Treatment options for adrenoleukodystrophy (ALD) are limited. Dietary treatment is with Lorenzo's oil. For the childhood cerebral form, stem cell transplant and gene therapy are options if the disease is detected early in the clinical course. Adrenal insufficiency in ALD patients can be successfully treated. (Wikipedia)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002356

FooDB ID

FDB004035

Phenol Explorer ID

Not Available

KNApSAcK ID

C00035114

BiGG ID

1459812

BioCyc ID

Not Available

METLIN ID

6642

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

YMDB00785

ECMDB ID

Not Available

References

Synthesis Reference

Tsuji S; Sano T; Ariga T; Miyatake T Increased synthesis of hexacosanoic acid (C23:0) by cultured skin fibroblasts from patients with adrenoleukodystrophy (ALD) and adrenomyeloneuropathy (AMN). Journal of biochemistry (1981), 90(4), 1233-6.

MSDS

Link

General References

1. Tsuji S; Sano T; Ariga T; Miyatake T Increased synthesis of hexacosanoic acid (C23:0) by cultured skin fibroblasts from patients with adrenoleukodystrophy (ALD) and adrenomyeloneuropathy (AMN). Journal of biochemistry (1981), 90(4), 1233-6.

2. Tsuji S; Sano T; Ariga T; Miyatake T Increased synthesis of hexacosanoic acid (C23:0) by cultured skin fibroblasts from patients with adrenoleukodystrophy (ALD) and adrenomyeloneuropathy (AMN). Journal of biochemistry (1981), 90(4), 1233-6.

3. Moser HW, Moser AB, Powers JM, Nitowsky HM, Schaumburg HH, Norum RA, Migeon BR: The prenatal diagnosis of adrenoleukodystrophy. Demonstration of increased hexacosanoic acid levels in cultured amniocytes and fetal adrenal gland. Pediatr Res. 1982 Mar;16(3):172-5.

4. Dhaunsi GS, Kaur J, Alsaeid K, Turner RB, Bitar MS: Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. Cell Biochem Funct. 2005 Jan-Feb;23(1):65-8.

5. Deon M, Wajner M, Sirtori LR, Fitarelli D, Coelho DM, Sitta A, Barschak AG, Ferreira GC, Haeser A, Giugliani R, Vargas CR: The effect of Lorenzo's oil on oxidative stress in X-linked adrenoleukodystrophy. J Neurol Sci. 2006 Sep 25;247(2):157-64. Epub 2006 Jun 5.

6. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.

7. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1911873

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19135040

Hexacosanoic acid (CHEM003246)

Structure for CHEM003246: Hexacosanoic acid