우르솔산

우르솔산
우르솔산 구조식 이미지
카스 번호:
77-52-1
한글명:
우르솔산
동의어(한글):
우르솔산;우르솔릭애씨드
상품명:
Ursolic acid
동의어(영문):
Ursolic;3BETA-HYDROXY-12-URSEN-28-IC ACID;PRUNOL;SAGE EXTRACT;MALOL;URSON;MICROMEROL;Uosolic Acid;Ursoliic acid;3beta-hydroxyurs-12-en-28-oic acid
CBNumber:
CB7470516
분자식:
C30H48O3
포뮬러 무게:
456.71
MOL 파일:
77-52-1.mol
MSDS 파일:
SDS

우르솔산 속성

녹는점
292 °C (dec.) (lit.)
알파
59 º (c=0.3, pyridine)
끓는 점
502.79°C (rough estimate)
밀도
1.0261 (rough estimate)
굴절률
1.4940 (estimate)
저장 조건
2-8°C
용해도
DMSO에 용해됨(가온 시 최대 25mg/ml)
물리적 상태
결정질 분말 또는 바늘
산도 계수 (pKa)
4.68±0.70(Predicted)
색상
흰색에서 황백색까지
수용성
불용성
Merck
14,9890
BRN
2228563
안정성
제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO의 솔루션은 -20°C에서 최대 2개월 동안 보관할 수 있습니다.
LogP
8.731 (est)
CAS 데이터베이스
77-52-1(CAS DataBase Reference)
EPA
Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)- (77-52-1)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 36/37/38
안전지침서 24/25-36-26
WGK 독일 -
RTECS 번호 YU9520000
F 고인화성물질 10-23
HS 번호 29181990
유해 물질 데이터 77-52-1(Hazardous Substances Data)
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 GHS hazard pictograms P264, P270, P301+P312, P330, P501
예방조치문구:
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

우르솔산 C화학적 특성, 용도, 생산

화학적 성질

white to light yellow crystal powde

용도

Ursolic Acid is a Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties. It inhibits endothelial cell proliferation and migration (IC50=5 μM) and angiogenesis. Promotes skeletal muscle rejuvenation via enhanced SIRT1 expression. Induces apoptosis in malignant mesothelioma cells. Ursolic acid protects against muscle atrophy and boosts muscle growth (see also tomatidine T538500).

주요 응용

ursolic acid helps maintain the look and feel of the skin, acts as a perfume and helps mask odor. Therapeutic benefits in skin care include anti-inflammatory activity. ursolic acid has demonstrated anti-microbial, anti-bacterial, and anti-fungal action as well.

정의

ChEBI: Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane.

일반 설명

Ursolic acid (UA) is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits anti-bacterial, anti-cancer, anti-oxidative and anti-inflammatory effects. It can also promote neuroregeneration after peripheral nerve injury. UA can enhance sleep duration by activating the GABAergic neurotransmitter system. [GABA= γ-aminobutyric acid]

Anticancer Research

It is a triterpenoid, derived from basil, and suppresses the activation of NF-κB byinhibiting a kinase that activates NF-κB(IKK) (Aggarwal and Shishodia 2004). It suppresses tumorigenesis, tumor promotion, and angiogenesis by downregulationof the expression of lipoxygenases (LOX), MMP-9, and COX-2. It is reported toinduce apoptosis in breast cancer, melanoma, hepatoma, prostate cancer, andacute myelogenous leukemia by preventing replication of DNA, inhibition of proteintyrosine kinases, activation of caspases, induction of calcium release, anddownregulating apoptosis gene cellular inhibitor. Ursolic acid inhibits IκBαkinase activity, degradation of IκBα, phosphorylation, NF-κB-dependent reportergene expression, p65 nuclear translocation, and p65 phosphorylation. Inhibitionof NF-κB leads to the reduction of cyclin D1, COX-2, and MMP9 expression.This downregulates STAT-3 activation and its regulated gene products such ascyclin D1, Mcl-1, Bcl-xL, survivin, Bcl-2, and VEGF. It also induces the expressionof tyrosine phosphatase SHP-1 protein and of mRNA (Aggarwal et al. 2008;Hsu et al. 2004).

부작용

Adverse effects of Ursolic acid include reduction of sperm viability and inhibition of spermatogenesis, leading to infertility. Ursolic acid is capable of inducing endothelial cell death at concentrations above 12.5uM, and the mechanism of death is related to apoptosis. In addition, it also appears to cause DNA strand breaks.

Cytotoxicity

IC50 (μg/mL): 6.7 (518A2), 5.3 (A2780), 7(A549), 6.4 (FaDu), 4.8 (HT29), 5.8(MCF-7), 8.5 (NIH3T3) (Wiemann et al.2016)
IC50 (μg/mL): 12.38 (MGC-803),17.12(HCT-116), 13.39 (T24), 13.81(HepG2), 16.36 (A549), >45.7 (HL-7702)(Hua et al. 2015).

우르솔산 준비 용품 및 원자재

원자재

준비 용품


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