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Catechin

HCID 9064
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
100786-01-4
Standard SMILES
Oc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@@H](O)C2
InChIKey
PFTAWBLQPZVEMU-DZGCQCFKSA-N
Molecular formula
C15H14O6
Average molar mass
290.27 g/mol
Monoisotopic mass
290.07903816

Overview

(+)-catechin is the (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. It has a role as an antioxidant and a plant metabolite. It is an enantiomer of a (-)-catechin.

Names & identifiers

Preferred name
Catechin
IUPAC
(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
English name
Cianidanol
Molecular formula
C15H14O6
Molecular weight
290.27

Names & synonyms

CianidanolCATECHIN154-23-4Catechuic acidD-CatechinCatechinic acidCianidol(+)-CatecholD-Catechol(+)-CyanidanolD-(+)-Catechin(2R,3S)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol
Show more names
(+)-catechinCatechinecatergenCianidanocatechinicacid(2R,3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triolkb-53
Cianidanolum(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triolNSC-2819Catechin, d-3,3',4',5,7-Flavanpentol(+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-trans)-8R1V1STN48

Database identifiers

CAS
100786-01-4、154-23-4、7295-85-4
PubChem CID
9064
DTXSID
DTXSID001349029
ChEMBL
CHEMBL206452、CHEMBL311498
ChEBI
CHEBI:15600
UNII
5J4Y243W61、8R1V1STN48
EC Number
205-825-1、230-731-2
Nikkaji
J9.391B

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
110 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
21
Formal charge
0
Complexity
364

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavans, Flavanols and Leucoanthocyanidins [PK1202]
SpringerMaterials PropertiesChemical shift
LogP · 2 items

0.51

1.31

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point214 °C
Physical DescriptionSolid
Collision Cross Section · 2 items

159.96 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

159.4 Ų [M-H]-

Physicochemical properties

Melting point
175 · 175-177 °C (anhydrous)(lit.)
alpha
18 · D18 +16 to +18.4°
Boiling point
352.36 °C · 352.36°C (rough estimate)
Density
1.2451 · 1.2451 (rough estimate)
refractive index
1.4359 · 1.4359 (estimate)
storage temp.
2 · 2-8°C
solubility
DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated, Heated)
form
Solid
pka
9.54 · 9.54±0.10(Predicted)
color
Light Orange to Light Brown
Merck
14 · 14,1902
Major Application
food and beverages
InChI
1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
InChIKey
PFTAWBLQPZVEMU-DZGCQCFKSA-N
SMILES
O[C@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3ccc(O)c(O)c3
LogP
0.51 · 0.510
CAS DataBase Reference
154 · 154-23-4
NCI Dictionary of Cancer Terms
catechin
FDA UNII
8 R1V1STN48 · 8R1V1STN48
EPA Substance Registry System
2 H-1-Benzopyran-3,5,7-triol, · 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)- (154-23-4)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs
Respiratory system
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
3450000 · DJ3450000
F
8 · 8-10-23
HS Code
29329990 · 29329990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Toxicity
50 oral · LD50 oral in rat: > 10gm/kg

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 · 6 items

This chemical does not meet GHS hazard criteria for 83% (39 of 47) of all reports.

Warning

H315 (17%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, 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 47 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Hazard information

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Skin Irrit. 2 (17%)

Safety data

F
8-10-23
wgk
3
rtecs
DJ3450000
hs_code
29329990
Toxicity
LD50 oral in rat: > 10gm/kg
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H315-H319-H335
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Tissue LocationsBladder
Applications · 4 items

Usesprocollagen production inhibitoe, hepatoprotectant

UsesCianidanol, also known as (+)-catechin; (+)-3,3′4′,5,7-flavanepentol; 3,3′,4′, 5,7-pentahydroxyflavane, [R,3S]-2-[3,4-dihydroxyphenyl]-3,4-dihydro-1[2H]- benzopyran-3,4,7-triol, or 2-(3,4-dihydroxyphenyl)-3,4-dihydro-(2r-trans)-2h- 1-benzopyran-7-triol, is a flavonoid associated with a variety of blood disorders. An association of cianidanol and immune hemolytic anemia and thrombocytopenia has been suggested in numerous case reports. In several reports, the presence of flavonoid-dependent antibodies against red blood cells is evident with cianidanol combining with erythrocyte membranes and inducing development of autoantibodies and antibodies.Several patients had platelet antibodies with increased serum-bindable IgG values without the presence of cianidanol and several with high platelet-associated IgG levels.Antibodies against cianidanol were not detectable in certain cases.The hemolytic anemia caused acute renal failure in some patients and can be life threatening, leading to fatalities. Upon cessation of treatment with cianidanol, hematology appears to return to normal over time.These side effects do not appear to be specific to cianidanol as the formation of IgE and IgG antibodies to troxerutin (Venoruton) and silymarin (Kegalon) was also evident with patients presenting with fever, skin eruptions, and intravascular hemolysis often demonstrating high IgG titers.Furthermore, cianidanol-induced hemolysis might also occur after sensitization by other flavonoids including rutin.

UsesLabelled (+)-Catechin (C217500). (+)-Catechin is a flavonoid found primarily in higher woody plants as (+)-Catechin along with (-)-Epicatechin (cis form). Antidiarrheal.

General Description(+)-Catechin is an important beneficial compound, belonging to the flavonoid class, which is present abundantly in red wine.

Upstream & downstream products

Downstream products

CACAO PIGMENTProcyanidin B1

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [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(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
TransMIT GmbH PlantMetaChem+49-172-1024293 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Labex Corporation+91-11-26135922 or +91-11-46160359 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [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]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
北京诺其雅盛生物科技有限公司4000-819-385 010-62329685 13718666987
九鼎化学(上海)科技有限公司4009209199 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
成都润泽本土化工有限公司028-88469284 18000562381 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
上海西陇生化科技有限公司021-52907766-8042
广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]
上海前衍生物科技有限公司02781293128 · [email protected]

Additional notes

DefinitionChEBI: The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes