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베툴린

Betulin

HCID 221023
노트반응

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기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
473-98-3
표준 SMILES
C=C(C)C1CCC2(CO)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C12
분자식
C30H50O2
평균 분자량
442.72 g/mol

이름 및 식별자

우선 이름
Betulin
현지명
베툴린
영어명
Betulin
분자식
C30H50O2
분자량
442.72

이름 및 동의어

베툴린TROCHOLBetulineBirch bark extractBETULINOLbetula camphorBetulinic alcohol(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-olBetuLetulinBETULIN

데이터베이스 식별자

CAS
473-98-3
PubChem CID
221023

물성

물리화학적 성질

녹는점
256 · 256-257 °C(lit.)
끓는 점
493.26 °C · 493.26°C (rough estimate)
밀도
0.9882 · 0.9882 (rough estimate)
굴절률
1.5045 · 1.5045 (estimate)
저장 조건
2 · 2-8°C
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨, 가열)
물리적 상태
황백색 분말
산도 계수 (pKa)
15.1 · 15.10±0.10(Predicted)
색상
옅은 갈색에서 베이지색까지
Merck
14 · 14,1189
안정성
흡습성
주요 응용
음식 및 음료
화장품 원료 기능
피부 컨디셔닝
InChIKey
FVWJYYTZTCVBKE-ROUWMTJPSA-N
SMILES
[H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]5(CO)CC[C@@H](C(C)=C)[C@]25[H]
LogP
8.607 · 8.607 (est)
NIST
Betulin(473-98-3)

화학적 성질

crystals

안전 및 규제

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

안전 데이터

wgk
3
rtecs
OK5755000
HS 번호
29181985
risk_code
36/37/38-20/21/22-68/20/21/22-68
hazard_code
Xn,Xi
safety_code
36/37-36-26
Hazard Classifications
STOT SE 2
스토리지 클래스
11 - Combustible Solids

화학 및 산업

응용 분야 · 3건

개요Sterol regulatory element binding protein 2 (SREBP-2) regulates cholesterol synthesis by activating the transcription of genes for HMG-CoA reductase and other enzymes of the cholesterol synthetic pathway. When cellular sterol levels are high, SREBP is bound by SCAP and Insig to ER membranes as a glycosylated precursor protein. Upon cholesterol depletion, the protein is cleaved to its active form and translocated into the nucleus to stimulate transcription of genes involved in the uptake and synthesis of cholesterol. Betulin, the precursor of betulinic acid, is a pentacyclic triterpene found in the bark of birch trees. Betulin inhibits the SREBP-driven pathway of cholesterol and fatty acid biosynthesis by promoting SCAP–Insig binding which prevents the activation and release of SREBP-2 from the ER. At 15-30 mg/kg/day, betulin has been shown to decrease lipid levels and increase insulin sensitivity in mice fed a western-type diet. In an atherosclerosis disease model, 30 mg/kg/day betulin can reduce the size and improve the stability of atherosclerotic plaques in LDLR-knockout mice. At 2.5-5 μg/ml betulin, in combination with cholesterol, demonstrates anticancer effects by inducing apoptosis in Jurkat cells, A549 lung carcinoma cells, and HeLa cervical carcinoma cells.

용도Betulin may be used in the preparation of betulinic acid, which shows anti-HIV, antimalarial and anti-inflammatory activities.

일반 설명A cell-permeable pentacyclic triterpenoid from birch bark extract that interacts with SCAP (SREBP cleavage activating protein) and prevents SREBP (sterol regulatory element-binding protein) Golgi proteolytic activation (1 to 13.55 μM in Rat hepatocytes CRL-1601) via a similar mechanism as oxysterols by inducing the association of SCAP with Insig-1 (insulin-induced gene-1), thereby causing SCAP-SREBPs complex ER retention. Unlike oxysterols, Betulin does not activate LXR to induce concomitant HMGCR (HMG-CoA reductase) degradation and SREBP-1 up-regulation. While both Betulin and HMGCR inhibitor Lovastatin (Cat. No. 438185) inhibit cellular cholesterol synthesis (by ~70% in CRL-1601 cultures with respective compound at 13.55 and 1 μM concentration), only Betulin suppresses cellular fatty acid synthesis (by ~55% at 13.55 μM in CRL-1601). Betulin is shown to exhibit comparable in vivo efficacy as Lovastatin (both dosed at 30 mg/kg/day with chow) in ameliorate high fat/cholesterol diet-induced obesity (% fat/lean tissue ratio increase from non-fat diet mice = 167, 44, and 33 in mice consuming fat diet alone, with Lovastatin, with Betulin, respectively). However, only Betulin is demonstrated to lower fasting blood glucose and insulin levels and reduce fat cell size in white adipose tissue in high fat diet mice. Fatostatin (Cat. No. 341329) in comparison does not target SCAP via sterol-binding site, nor does it induce SCAP binding to Insig-1.

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화합물 노트

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이 페이지에서기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

상·하류 제품 정보

상류 원료

베툴린-3-아세테이트BETULIN DIACETATE에틸알코올Betulinic acid톨루엔수산화칼륨

하류 제품

betulonic aldehyde

공급사100 곳

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추가 설명

정의ChEBI: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.