25-HYDROXYCHOLESTEROL

한글명:25-HYDROXYCHOLESTEROL

카스 번호2140-46-7

상품명:25-HYDROXYCHOLESTEROL

CBNumberCB7412673

분자식C27H46O2

포뮬러 무게402.65

MOL 파일2140-46-7.mol

화학적 성질

녹는점	177-179 °C
끓는 점	513.1±23.0 °C(Predicted)
밀도	1.03±0.1 g/cm3(Predicted)
저장 조건	-20°C
용해도	클로로포름: 50mg/mL, 투명, 무색 내지 약간 노란색
물리적 상태	고체
물리적 상태	단단한 모양
산도 계수 (pKa)	15.03±0.70(Predicted)
색상	흰색 또는 연한 노란색
Merck	13,4846
BRN	3161259
안정성	제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°에서 최대 3개월 동안 보관할 수 있습니다.
InChIKey	INBGSXNNRGWLJU-ZHHJOTBYSA-N

위험 및 안전 성명

위험품 표기

위험 카페고리 넘버

20/21/22-36/37/38-48

안전지침서

26-36-45

WGK 독일

HS 번호

29062990

NFPA 704:

	0
3		0

그림문자(GHS)

25-HYDROXYCHOLESTEROL 화학적 특성, 용도, 생산

개요
25-hydroxy Cholesterol is an oxysterol. It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection. 25-hydroxy Cholesterol suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi. It inhibits IgA class switching induced by LPS and various cytokines in B cells (IC₅₀ = ~50 nM). 25-hydroxy Cholesterol inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC₅₀ = 3.675 μM) and reduces increases in viral protein production in infected Vero cells when used prior to infection. It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day. Serum levels of 25-hydroxy cholesterol are increased in mice expressing human angiotensin-converting enzyme 2 (hACE2), the functional receptor for SARS-CoV-2, in a model of SARS-CoV-2 infection and in a patient with COVID-19, the primarily respiratory disease caused by SARS-CoV-2.
화학적 성질
Off-White Solid
용도
25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.
일반 설명
25-hydroxy-cholesterol is a side chain substituted oxysterol. Avanti′s unique sterol reverses cataracts in mice. Gestwicki′s team ...... settled on compound 29, a steroid found naturally in the bloodstream but not in the lens, which has no blood supply. Mice with age-related and hereditary cataracts received drops in the right eye, whereas the left eye went untreated. After just a few weeks, the treated eye was visibly clearer, says Gestwicki, who conducted the work while at the University of Michigan. Cataract severity is measured on a scale of zero to four, with four being the worst case. On average, mice in the study had about a one-grade improvement in cataract severity after 4 weeks of treatment. Science DOI: 10.1126/science.aad7400 It has been recently shown that activation of a macrophage toll-like receptor (TLR) by microbial antigens induces synthesis of 25-hydroxycholesterol, and that this oxysterol potently suppresses IgA production.
Purification Methods
25-Hydroxycholesterol forms colourless needles from MeOH [Schwartz Tetrahedron Lett 22 4655 1981]. The 3acetoxy derivative has m 142-142.8o (from Me2CO) and [] D -40.4o (c 2, CHCl3). The 3,25-diacetoxy derivative has m 119-120.5o (from MeOH) and [] 25D -35.5o (CHCl3). [Dauben & Bradlow J Am Chem Soc 72 4248 1950, Ryer et al. J Am Chem Soc 72 4247 1950, Beilstein 6 IV 6437.]

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