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디오스민

Diosmin

HCID 5281613
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
520-27-4
표준 SMILES
COc1ccc(-c2cc(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3o2)cc1O
InChIKey
GZSOSUNBTXMUFQ-YFAPSIMESA-N
분자식
C28H32O15
평균 분자량
608.5 g/mol
단동위원소 질량
608.17412032

개요

Diosmin is a disaccharide derivative that consists of diosmetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and an anti-inflammatory agent. It is a monomethoxyflavone, a rutinoside, a dihydroxyflavanone, a glycosyloxyflavone and a disaccharide derivative. It is functionally related to a diosmetin.

이름 및 식별자

우선 이름
Diosmin
IUPAC
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
현지명
디오스민
영어명
Diosmin
분자식
C28H32O15
분자량
608.55

이름 및 동의어

diosmin520-27-4BarosminVenosmineDiosmineFlebostenToveneVen-DetrexDiovenorBuchu ResinLitosmilflebosmil
이름 더 보기
디오스민다이오스민DIOSMETIN-7-O-RUTINOSIDEHesperedinDIOSIMINSiF6Rubber powderDaflonDiosmin CRSDioveniosmin
DiosminumFlebavenaDiosmetin 7-O-rutinosideDiosvenFlebavenHemervenInsuvenVarinon

데이터베이스 식별자

CAS
520-27-4
PubChem CID
5281613
DTXSID
DTXSID4045892
ChEMBL
CHEMBL231884
ChEBI
CHEBI:4631
UNII
7QM776WJ5N
EC Number
208-289-7
Nikkaji
J6.600A

물성

구조 계산 물성

XLogP
-0.8
극성 표면적
234 Ų
수소 결합 공여자 수
8
수소 결합 수용자 수
15
회전 가능 결합 수
7
무거운 원자 수
43
형식 전하
0
복잡도
995

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
CosmeticsAntioxidant
LogP0.14
Boiling Point926.8±65.0
Melting Point277-278
Dissociation Constants6.10±0.40
Collision Cross Section · 2건

243.33 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

242.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
277 · 277-278°C
끓는 점
926.8 · 926.8±65.0 °C(Predicted)
밀도
1.68 · 1.68±0.1 g/cm3(Predicted)

안전 및 규제

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

GHS 분류

GHS Classification · 3건

This chemical does not meet GHS hazard criteria for 90.8% (89 of 98) of all reports.

Not Classified

Aggregated GHS information provided per 98 reports by companies from 2 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory InformationStatus: Active Update: 13-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21071
Hazard Classes and CategoriesNot Classified

안전 데이터

wgk
3
HS 번호
29381000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-36/37-24/25
기존화학 물질
KE-34297
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 2건

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingDiosmin binds to serum albumin.
Pharmacodynamics · 1건

Diosmin is a venoactive drug supporting circulatory health through various actions on blood vessels; it supports lymphatic drainage and improves microcirculation while increasing venous tone and elasticity. For these reasons, diosmin is frequently taken by individuals with chronic venous disease to support vascular health and has been demonstrated to improve quality of life. In addition to the above effects, diosmin exerts antioxidant activity and scavenges oxygen free radicals, reducing levels of oxidative stress normally detected through biomarkers such as prostaglandins isoprostane precursors. In one clinical study, mean content of TNF alpha, VEGF-C, VEGF-A IL-6, in addition to FGF2 were decreased by after the therapy with diosmin; findings were statistically significant. Additionally, a decrease in edema and mean leg circumference of patients taking diosmin for three months was observed in a clinical study. Diosmin has been demonstrated to enhance the metabolism of glucose in diabetic disorders.

Mechanism of Action · 1건

Diosmin helps to maintain circulatory system structure and function, particularly vein strength and competence. The molecular mechanism of action of diosmin has not been established. Several resources indicate that diosmin binds to the aryl hydrocarbon receptor, however clinical relevance to vascular function is unknown. One study demonstrates that oral diosmin exerts effects on the in vitro metabolism of noradrenaline by varicose veins, potentially benefitting vascular health.

Biological Half-LifeDiosmin half-life ranges from 26 to 43 hours. One study using a liquid chromatography with tandem mass spectrometry (LC-MS/MS) method after a single 900 mg dose of diosmin demonstrated a half-life of 60.2±85.7 hours in healthy volunteers.
Metabolism/MetabolitesDegradation products of diosmin such as alkyl-phenolic acids confirm a metabolic pattern similar to that of other flavonoids.

관련 반응

3건
반응 기록 만들기
HRID 61526 반응식
HRID 61526반응물로uspto-grants-2016_09
HRID 2222318 반응식
HRID 2222318반응물로uspto-grants-2008_05
HRID 2230904 반응식
HRID 2230904생성물로uspto-grants-2002_07

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
증기압
0 Pa · 0Pa at 20℃
저장 조건
2 · Sealed in dry,2-8°C
용해도
물에 거의 녹지 않으며, 디메틸설폭사이드에 녹고, 알코올에는 거의 녹지 않습니다. 알칼리 수산화물의 묽은 용액에 용해됩니다.
물리적 상태
Solid
산도 계수 (pKa)
6.1 · 6.10±0.40(Predicted)
색상
페일베이지부터 브라운까지
수용성
DMSO(50mg/ml), 물(25°C에서 122mg/ml) 및 에탄올(25°C에서 <1mg/ml)에 용해됩니다.
Merck
14 · 14,3297
주요 응용
음식 및 음료
화장품 원료 기능
항산화제
InChIKey
GZSOSUNBTXMUFQ-YFAPSIMESA-N
SMILES
COc1ccc(cc1O)C2=CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2
LogP
0.14 at · 0.14 at 20℃
화학적 성질 · 1건

Diosmin is a natural flavonoid mainly present in the peel of some citrus fruits, such as oranges and lemons. Flavonoids are anti-inflammatory plant compounds that protect your body from free radicals and other unstable molecules. The most prevalent uses for Diosmin include hemorrhoids and leg sores caused by poor blood flow. Diosmin was first found in 1925 in the wort plant and has since been used as a natural treatment for hemorrhoids, varicose veins, venous insufficiency, leg ulcers, and other circulatory issues.

Absorption, Distribution and Excretion · 3건

Diosmin is rapidly absorbed in the gastrointestinal tract. After a 900 mg single oral dose in a study using liquid chromatography with tandem mass spectrometry (LC-MS/MS) method, Cmax was 4.2±3.8 ng·mL-1, Tmax was 18.7±9.9 hours, and AUC0~96 was 185.4±166.2 ng·mL-1 in healthy volunteers. Another pharmacokinetic study of 5 adults revealed a Cmax of 417±94.1 ng/dL.

Pharmacokinetic data show absence of urinary elimination for diosmin and its aglycone diosmetin. Minor metabolites are found to be eliminated in the urine as glucuronic acid conjugates.

A pharmacokinetic study of 5 adults revealed a volume of distribution of 62.1±7.9 L.

용도 및 제조

UsesUse (kg) in France (2004): 373544
Use ClassificationCosmetics -> Antioxidant
응용 분야 · 3건

개요Diosmin was separated from the root of Scrophularia nodosa L. in 1925. The root of Scrophularia nodosa L. has the function of nourishing, reducing fever, relieving internal heat, and detoxicating. It was firstly recorded in the Shen Nong’s Classic of Materia Medica, as a class of middle-grade drug and is currently recorded in the Ch.P 2015, Volume I. The natural resource was abundant in China, mainly provided from Zhejiang, Sichuan, Hubei, Anhui, and Jiangsu provinces. In the clinical practice, Scrophularia nodosa L. was employed to eliminate pathogenic heat from the blood. In the clinical indication, diosmin was mainly applied to treat fever, polydipsia, maculitis, gingivitis, amygdalitis, laryngopharyngitis, acute lymphadenitis, etc. It also has the biological function of antiplatelet aggregation and antitumor. The chemical components include iridoids, phenylpropanoid glycoside, flavonoids, and fatty acids.

역사Diosmin was firstly introduced as a medicine in 1969. It was launched in France in 1987 with the product name “Alvenor.” As the protecting agent for blood vessel and therapeutic agent for chronic venous disease, diosmin has been used for over 30years in EuropeDiosmin is a typical flavonoid. It could be prepared from natural resources or semisynthesized from the natural product hesperidin by dehydrogenation reaction.

용도Diosmin is an agonist of the aryl hydrocarbon receptor (AhR) and exhibits anti-proliferative and anti-inflammatory. It is used in the treatment of venous disease, i.e., chronic venous insufficiency (CVI) and hemorrhoidal disease (HD). Diosmin also reduces capillary hyperpermeability and expression of endothelial adhesion molecules (ICAM1, VCAM1). It effectively inhibits the P-glycoprotein (Pgp)-mediated efflux in cells.

상·하류 제품 정보

상류 원료

수산화나트륨아세트산(빙초산)비타민 P무수초산

공급사100 곳

北京华美互利生物化工010-56205725 · [email protected]
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AN PharmaTech Co Ltd86(21)68097365 · [email protected]
추가 설명 · 1건

정의ChEBI: Diosmin is a disaccharide derivative that consists of diosmetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and an anti-inflammatory agent. It is a glycosyloxyflavone, a rutinoside, a disaccharide derivative, a monomethoxyflavone and a dihydroxyflavanone. It derives from a diosmetin.