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Anacardic Acid

HCID 167551
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
11034-77-8
표준 SMILES
CCCCCCCCCCCCCCCc1cccc(O)c1C(=O)O
InChIKey
ADFWQBGTDJIESE-UHFFFAOYSA-N
분자식
C22H36O3
평균 분자량
348.5 g/mol
단동위원소 질량
348.26644501

개요

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.

이름 및 식별자

우선 이름
Anacardic Acid
IUPAC
2-hydroxy-6-pentadecylbenzoic acid
영어명
6-pentadecylsalicylic acid
분자식
C22H36O3
분자량
348.52

이름 및 동의어

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
이름 더 보기
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

데이터베이스 식별자

CAS
11034-77-8、16611-84-0
PubChem CID
167551
DTXSID
DTXSID00168078
ChEMBL
CHEMBL33778、CHEMBL455368

물성

구조 계산 물성

XLogP
9.5
극성 표면적
57.5 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
15
무거운 원자 수
25
형식 전하
0
복잡도
329

실험 및 물리화학적 성질

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

물리화학적 성질

녹는점
90 · 90-91℃
끓는 점
474.8 · 474.8±33.0 °C(Predicted)
밀도
1.002 · 1.002
저장 조건
-20 °C · -20°C
용해도
20 mg/mL · DMSO: ≥20mg/mL
산도 계수 (pKa)
3.08 · 3.08±0.30(Predicted)
물리적 상태
흰색 고체
색상
흰색에서 베이지색
안정성
1 · 제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
주요 응용
음식 및 음료
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)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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]

유해성 정보

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

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

안전 데이터

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

화학 및 산업

약리 정보

Cellular LocationsMembrane
응용 분야 · 3건

개요Anacardic 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.

용도Anacardic 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]

일반 설명A cell-permeable ginkgolic acid (Cat. No. 345887) analog that inhibits protein SUMO (Cat. Nos. 662037, 662039, and 662042) modification (IC50 = 2.2 μM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 (Cat. Nos. 662073 and 662074) and interfering with E1-SUMO intermediate formation. Both anacardic acid and ginkgolic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although anacardic acid is shown to inhibit p300 (Cat. No. 506200) and PCAF (Cat. No. 124026) histone acetyltransferase activities in cell-free acetylase assays (by 82% and 86%, respectively, at 10 μM). Also reported to inhibit the activity of prostaglandin synthase, tyrosinase, and lipoxygenase, as well as to enhance Aurora kinase A (Cat. No. 481413), but not Aurora kinase B, autophosphorylation and kinase activity by inducing conformation change and enhancing ATP binding.

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
ChEBI
CHEBI:2696
UNII
8H693KBS2W
EC Number
234-268-7、683-602-1
Nikkaji
J167.336J
InChIKey
ADFWQBGTDJIESE-UHFFFAOYSA-N
SMILES
C(O)(=O)C1=C(CCCCCCCCCCCCCCC)C=CC=C1O
LogP
9.96 · 9.960 (est)

공급사110 곳

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