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Hexacosansure

Hexacosanoic Acid

HCID 10469
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Grundinformationen

CAS
506-46-7
Standard-SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O
InChIKey
XMHIUKTWLZUKEX-UHFFFAOYSA-N
Summenformel
C26H52O2
Durchschnittliche Molmasse
396,7 g/mol
Monoisotopische Masse
396,3967309

Überblick

Hexacosanoic acid is a 26-carbon, straight-chain, saturated fatty acid. It is a fatty acid 26:0, a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a cerotate.

Namen und Bezeichner

Bevorzugter Name
Hexacosanoic Acid
IUPAC
hexacosanoic acid
Lokaler Name
Hexacosansure
Englischer Name
Hexacosanoic acid
Summenformel
C26H52O2
Molmasse
396.69

Namen und Synonyme

HEXACOSANOIC ACID506-46-7Cerotic acidCeratinic acidCeric acidCerinic acidn-Hexacosanoic acidCerylic acidCerotinic acidD42CQN6P36C26:0NSC-4205
Weitere Namen anzeigen
Hexacosanic acidNSC 4205CericacidC26:0 ACIDceroticaciCerinicacid
DTXSID7075050CHEBI:31009RefChem:785921Very Long Chain Fatty AcidC26:0 (VLCFA)DTXCID2040862CHEBI:27283208-040-2

Datenbank-Bezeichner

CAS
506-46-7
PubChem CID
10469
DTXSID
DTXSID7075050
ChEMBL
CHEMBL464787
ChEBI
CHEBI:31009
UNII
D42CQN6P36
EC Number
208-040-2
Nikkaji
J95.914F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
11,8
Polarare Oberfläche (TPSA)
37,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
24
Schwere Atome
28
Formalladung
0
Komplexität
301

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Organic Acids
Lipids · 2 Einträge

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]

CosmeticsViscosity controlling
Melting Point88.5 °C
Physical Description · 2 Einträge

White solid; [Acros Organics MSDS]

Solid

Collision Cross Section · 2 Einträge

205.3 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]

201.57 Ų [M-H]- [CCS Type: TIMS; Method: single field calibrated]

Physikochemische Eigenschaften

Schmelzpunkt
84 · 84-88 °C
Siedepunkt
250 °C · 250 °C
Dichte
0.81 · 0.81

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.

Warning

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: Hexacosanoic acid

Hexacosanoic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Hexacosanoic acid: Human health tier I assessment
Hazards SummaryMay cause irritation; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Health Effects

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsAdrenal Gland
Cellular LocationsCytoplasm
Metabolite PathwaysAcylcarnitine Hexacosanoylcarnitine

Verwendung und Herstellung

UsesHexacosanoic acid is most commonly found in beeswax and carnauba wax (Wikipedia). It is also an endogenously produced metabolite found in the human body.
Use ClassificationCosmetics -> Viscosity controlling
Anwendungen · 1 Eintrag

VerwendenHexacosanoic acid may be used as a reference standard for the determination of hexacosanoic acid in human serum and plasma samples for the screening of peroxisomal disorders by gas chromatography-mass spectrometry (GC-MS) operating under selected-ion monitoring (SIM) modein biological samples by GC-MSin microalgal lipids by solid-phase extraction (SPE) followed by GC-MS analysisas a naphthoxyethyl derivative by high performance liquid chromatography (HPLC) coupled with fluorometric detection

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

HexacosanenitrileUndecanoic acid, 11-iodo-, methyl esterHexacosan-1-ol1-BrompentadecanMyristoyl chloride

Zugehörige Reaktionen

1
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 2201763
HRID 2201763als Eduktuspto-grants-2016_06

Notizen zur Verbindung

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Brechungsindex
1.4301 · 1.4301
Flammpunkt
110 ℃ · >110℃
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform (Slightly, Heated), Hexanes (Slightly, Heated)
pka
4.78 · 4.78±0.10(Predicted)
Aggregatzustand
Shiny Fluffy or Crystalline Powder
Farbe
White
BRN
1799681 · 1799681
Kosmetik-Inhaltsstoffe Funktionen
VISCOSITY CONTROLLING
InChI
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)
InChIKey
XMHIUKTWLZUKEX-UHFFFAOYSA-N
SMILES
C(O)(=O)CCCCCCCCCCCCCCCCCCCCCCCCC
LogP
12.47 · 12.470 (est)
CAS Datenbank
506 · 506-46-7(CAS DataBase Reference)
EPA chemische Informationen
Hexacosanoic acid (506-46-7)
· 1 Eintrag

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)

Exposure RoutesIngestion
Toxicity Summary · 1 Eintrag

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)

Signs and Symptoms · 1 Eintrag

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)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
-
hs_code
29159000
safety_code
22-24/25
Speicherklasse
11 - Combustible Solids
Ethanol
Nonan-1-ol

Nachgelagerte Produkte

Triacontan-1-olMethylhexacosanoatN-hexacosanoylphytosphingosineN-(Hexacosanoyloxy)succinimide

Ergänzende Hinweise

DefinitionChEBI: A 26-carbon, straight-chain, saturated fatty acid.