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Anacardic Acid

HCID 167551
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Grundinformationen

CAS
11034-77-8
Standard-SMILES
CCCCCCCCCCCCCCCc1cccc(O)c1C(=O)O
InChIKey
ADFWQBGTDJIESE-UHFFFAOYSA-N
Summenformel
C22H36O3
Durchschnittliche Molmasse
348,5 g/mol
Monoisotopische Masse
348,26644501

Überblick

Anacardic acid is a hydroxybenzoic acid that is salicylic acid substituted by a pentadecyl group at position 6. It is a major component of cashew nut shell liquid and exhibits an extensive range of bioactivities. It has a role as an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an anticoronaviral agent, an antibacterial agent, a neuroprotective agent, an anti-inflammatory agent, an apoptosis inducer, an EC 2.3.1.48 (histone acetyltransferase) inhibitor and a plant metabolite. It is a hydroxybenzoic acid and a hydroxy monocarboxylic acid. It is functionally related to a salicylic acid.

Namen und Bezeichner

Bevorzugter Name
Anacardic Acid
IUPAC
2-hydroxy-6-pentadecylbenzoic acid
Englischer Name
6-pentadecylsalicylic acid
Summenformel
C22H36O3
Molmasse
348.52

Namen und Synonyme

ANACARDIC ACIDCHEBI:269611034-77-8RefChem:5580116-(Pentadecyl)Salicylic AcidDTXSID808728682-hydroxy-6-pendadecylbenzoic acid234-268-7683-602-12-hydroxy-6-((8E,11E)-pentadeca-8,11,14-trien-1-yl)benzoic acid6-nonadecyl salicylic acid16611-84-0
Weitere Namen anzeigen
Anachardic acidNSC 623096NSC 333857NSC 229596Anacardic Acid 15:0(15:0)-Anacardic acidPENTADECYLSALICYLICACIDHodrogenated anacardic acid
2-Hydroxy-6-pentadecylbenzoic acid6-Pentadecylsalicylic acidGinkgolic acid C15:0Hydroginkgolic acid2-Hydroxy-6-pentadecyl-benzoic acidcyclogallipharic acidBenzoic acid, 2-hydroxy-6-pentadecyl-22:0-Anacardic acid

Datenbank-Bezeichner

CAS
11034-77-8、16611-84-0
PubChem CID
167551
DTXSID
DTXSID00168078

Eigenschaften

Berechnete Struktureigenschaften

XLogP
9,5
Polarare Oberfläche (TPSA)
57,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
15
Schwere Atome
25
Formalladung
0
Komplexität
329

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Polyketides [PK] -> Phenolic lipids [PK15] -> Anacardic acids and derivatives [PK1504]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point92.5 - 93 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
90 · 90-91℃
Siedepunkt
474.8 · 474.8±33.0 °C(Predicted)
Dichte
1.002 · 1.002
storage temp.
-20 °C · -20°C
Löslichkeit
20 mg/mL · DMSO: ≥20mg/mL
pka
3.08 · 3.08±0.30(Predicted)
Aggregatzustand
White solid
Farbe
white to beige
Stabilität
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

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 · 6 Einträge

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

Gefahrenhinweise

Regulatory InformationChemical: Anacardic acid
Hazard Classes and Categories · 2 Einträge

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

Sicherheitsdaten

wgk
3
risk_code
36
hazard_code
Xi
safety_code
26
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsMembrane
Anwendungen · 2 Einträge

BeschreibungAnacardic acid, isolated from cashew shells or several other medicinal plants, is the general name given to a family of four different 6-alkyl salicyclic acids having varying degrees of unsaturation in the 15-carbon alkyl chain. These compounds are associated with anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial activity. Literature frequently sites and gives the name anacardic acid to the completely-saturated compound (6-pentadecyl salicylic acid). Anacardic acid inhibits the histone acetyltransferase (HAT) activity of the transcription co-activators p300 and p300/CREB-binding protein-associated factor (PCAF) with IC50 values of 8.5 and 5 μM, respectively. At 25 μmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.

VerwendenAnacardic acid, isolated from cashew shells or several other medicinal plants, is the general name given to a family of four different 6-alkyl salicyclic acids having varying degrees of unsaturation in the 15-carbon alkyl chain. These compounds are associated with anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial activity. Literature frequently sites and gives the name anacardic acid to the completely-saturated compound (6-pentadecyl salicylic acid). Anacardic acid inhibits the histone acetyltransferase (HAT) activity of the transcription co-activators p300 and p300/CREB-binding protein-associated factor (PCAF) with IC50 values of 8.5 and 5 μM, respectively. At 25 μmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.[Cayman Chemical]

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL33778、CHEMBL455368
ChEBI
CHEBI:2696
UNII
8H693KBS2W
EC Number
234-268-7、683-602-1
Nikkaji
J167.336J
Major Application
food and beverages
InChI
InChI=1S/C22H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h15,17-18,23H,2-14,16H2,1H3,(H,24,25)
InChIKey
ADFWQBGTDJIESE-UHFFFAOYSA-N
SMILES
C(O)(=O)C1=C(CCCCCCCCCCCCCCC)C=CC=C1O
LogP
9.96 · 9.960 (est)
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