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2-[3-Hydroxy-5-[2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

HCID 393787
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
65914-17-2
Standard SMILES
OCC1OC(Oc2cc(O)cc(C=Cc3ccc(O)cc3)c2)C(O)C(O)C1O
InChIKey
HSTZMXCBWJGKHG-UHFFFAOYSA-N
Molecular formula
C20H22O8
Average molar mass
390.4 g/mol
Monoisotopic mass
390.13146766

Overview

2-[3-Hydroxy-5-[2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol is a glycoside and a stilbenoid.

Names & identifiers

Preferred name
2-[3-Hydroxy-5-[2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
IUPAC
2-[3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
English name
Polydatin
Molecular formula
C20H22O8
Molecular weight
390.38

Names & synonyms

65914-17-22-[3-hydroxy-5-[2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triolSCHEMBL3123046CHEBI:182492HMS3393A20HMS3656A15(2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-(4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol2-[3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triolNCI60_034425NCI60_0344263,4'-5-Trihydroxystilbene-3-EC-D-glucopyranosidePICEID
Show more names
PolydatinPolydatinePolydatainPolydatinum(E/Z)-PiceidPolydatin 98%Polydatin ,98%(Z/E-)-PolydatinPolydatin(Piceid)

Database identifiers

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
140 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
8
Rotatable bonds
5
Heavy atoms
28
Formal charge
0
Complexity
506

Physicochemical properties

Melting point
223 · 223-226 °C(lit.)
alpha
-55 · -55 º (c=1,acetone)
Boiling point
707.7 · 707.7±60.0 °C(Predicted)
Density
1.521 · 1.521±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly), Water (Slightly)
pka
9.31 · 9.31±0.10(Predicted)
form
White to off-white solid.
color
White to off-white solid.
optical activity
20 · [α]20/D 55°, c = 1 in acetone
BRN
54837 · 54837
Cosmetics Ingredients Functions
ANTIOXIDANT
InChI
InChI=1/C20H23O9/c21-10-15-16(24)17(25)18(26)19(28-15)29-20(27)8-12(7-14(23)9-20)2-1-11-3-5-13(22)6-4-11/h1-9,15-19,21-27H,10H2/b2-1+/t15-,16-,17+,18-,19+/s3
InChIKey
KRZZBNXOOOHROO-ONKCTLKBNA-N

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29389090
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302
Precautionary statements
P280-P305+P351+P338

Chemistry & industry

Applications · 5 items

DescriptionPolydatin (PD) is a major chemical component of Polygonum cuspidatum and it could also be found in a variety of other sources. PD is a polyphenol belonging to the chemical family of stilbenoids. Previous studies have shown that PD exhibits many pharmacological activities, including cardioprotective, neuroprotective, and antioxidative activities. With vascular dementia (VaD) rat models, PD markedly attenuated cognitive deficits. Biochemical analysis revealed that PD decreased the production of malondialdehyde (MDA) and significantly increased superoxide dismutase and catalase activities. Additionally, PD effectively alleviated the injuries of cultured neurons induced by oxygen–glucose deprivation. The therapeutic potential of PD for VaD seems related to its antioxidative activity and the direct protection of neurons. Furthermore, PD could also effectively inhibit the polymerization of amyloid-β peptides, which is a major mark in the progression of pathogenesis in Alzheimer’s disease (AD). These results suggest that PD is a promising drug candidate or nutraceutical for the treatment of VaD and AD.

Description3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside is a stilbene glucoside that has been found in V. vinifera and has diverse biological activities. It reduces the growth of SKOV3 ovarian cancer cell 3D aggregates in a concentration-dependent manner. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (10 and 20 μg/ml) inhibits IL-17 production in activated peripheral blood mononuclear cells (PBMCs). It inhibits the loss of glutathione peroxidase 4 (GPX4) activity induced by the ferroptosis inducer hemin in Neuro2a neuroblastoma cells. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (50 mg/kg) reduces escape latency in a rat model of vascular dementia induced by four-vessel occlusion (4-VO).

UsesPolydatin, a type of polyphenolic phytoalexin, has many physiological and pharmacological effects including anti-inflammatory and anti-oxidative activities. Polydatin is an effective candidate drug for the protection of photo-inflammation. Polydatin exhibits therapeutic potential for vascular dementia, most likely due to its anti-oxidant activity and the direct protection of neurons.

UsesTrans-piceid is a stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. It has a role as a metabolite, a potassium channel modulator, an anti-arrhythmia drug, a hepatoprotective agent, an antioxidant and a nephroprotective agent. It is a stilbenoid, a polyphenol, a beta-D-glucoside and a monosaccharide derivative. It derives from a trans-resveratrol.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
65914-17-2
PubChem CID
393787
ChEBI
CHEBI:182492
EC Number
683-198-7
SMILES
C(/C1=CC=C(O)C=C1)=C\C1C=C(O)C=C(O)(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=1 |&1:17,19,22,24,26,r|
LogP
0.412 · 0.412 (est)
CAS DataBase Reference
65914 · 65914-17-2(CAS DataBase Reference)
FDA UNII
261 C37CQ · XM261C37CQ
UNSPSC Code
41116107 · 41116107
NACRES
25 · NA.25
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
280 · P280-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids

UsesPolydatin is a Resveratrol glycoside and inhibitor of platelet aggregation.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
江苏星科元信息科技有限公司400-605-7200 15335295587 · [email protected]
陕西昊辰生物科技有限公司18710685966 18710685966 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
武汉卡诺斯科技有限公司027-83238443 15327105076 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
南京圣亿来化工有限公司19951936396 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
杭州璟皓生物科技有限公司(原河南辛迪加生物)17513242016 · [email protected]
长沙上禾生物科技有限公司0731-84213302 18975842720 · [email protected]
长沙禾普生物科技有限公司0731-88202122 13187036806;13187036806 · [email protected]
Aktin Chemicals, Inc.028-85159085 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
西安康培基生物科技有限公司86-029-85456576 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
武汉普洛夫生物科技有限公司17612776928 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
北京环宇世纪化学科技有限公司hysj_bj.com
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
上海纳谦化学科技有限公司13598610367 13598610367 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
ALB Technology Limited702-983-3769 · [email protected]
Lifome Technologies LLC+1 347 9183313 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
武汉峰耀同辉化学制品有限公司027-87466205 15377579727 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
武汉匠信生物科技有限公司19272768272 18007157445 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
康幸生物科技(上海)有限公司021-61556450 15800904410
Additional notes · 1 item

DefinitionChEBI: Trans-piceid is a stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. It has a role as a metabolite, a potassium channel modulator, an anti-arrhythmia drug, a hepatoprotective agent, an antioxidant, a nephroprotective agent and a geroprotector. It is a stilbenoid, a polyphenol, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a trans-resveratrol.