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(2R,4S,4aR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

HCID 378697
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
477-90-7
Standard SMILES
COc1c(O)cc2c(c1O)C1O[C@H](CO)C(O)[C@H](O)[C@H]1OC2=O
InChIKey
YWJXCIXBAKGUKZ-ACTMFFEGSA-N
Molecular formula
C14H16O9
Average molar mass
328.27 g/mol
Monoisotopic mass
328.07943208

Names & identifiers

Preferred name
(2R,4S,4aR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
IUPAC
(2R,4S,4aR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
English name
Bengenin
Molecular formula
C14H16O9
Molecular weight
328.27

Names & synonyms

NSC661749(2R,4S,4aR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-oneAKOS025311493(2R,3S,4S,4aS,10bR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-oneNCI60_021436Pyrano[3, 3,4,4a,10b-tetrahydro xy-2-(hydroxymethyl)-9-methoxy-, [2R-(2.alpha.,3.beta.,4.alpha.,4a.alpha.,10b.beta.)]BERGENINVakerinEngeninGoldateBengeninBergenit
Show more names
CUSCUTINAi Cha SuNSC 661749Bergenitol

Database identifiers

CAS
477-90-7
PubChem CID
378697

Properties

Computed structural properties

XLogP
-1
Topological polar surface area
146 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
9
Rotatable bonds
2
Heavy atoms
23
Formal charge
0
Complexity
458

Physicochemical properties

Melting point
237 · 237-240 °C(lit.)
alpha
18 · D18 -37.7° (c = 1.96 in ethanol); D24 -45.3° (c = 0.51 for anhydr in water)
Boiling point
386.03 °C · 386.03°C (rough estimate)
Density
1.3901 · 1.3901 (rough estimate)
refractive index
1.655 · 1.6550 (estimate)
storage temp.
-20 °C · -20°C
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
8.26 · 8.26±0.70(Predicted)
color
White to Off-White
λmax
277 nm · 277nm(EtOH)(lit.)
Major Application
metabolomicsvitamins, nutraceuticals, and natural products
Cosmetics Ingredients Functions
SKIN CONDITIONING
InChI
1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1

Safety & regulation

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

Safety data

wgk
3
rtecs
UQ0337200
hs_code
29329990
risk_code
36/37/38-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Applications · 4 items

DescriptionThe plant resources of bergenin are rich, mainly from Rock cabbage (Bergenia purpurascens) and thick leafy rock cabbage (Astilbe macroflora) from Saxifragaceae and the roots, stems, and leaves of bai liang jin (Ardisia crispa) from Ardisia japonica (Thunb.) Blume. In Chinese medicine Rock cabbage (Bergenia purpurascens) is the common folk medicine, with nourishing, stanching bleeding, relieving a cough, and other effects. Its earliest record is contained in the classified herbal in Qing Dynasty .There are ten kinds of Rock cabbage (Bergenia purpurascens) in Asia, mainly growing in East Asia, north of South Asia, and southeastern Central Asia. There are seven species (including three endemic species) in China, mainly distributed in Shaanxi (Qinling), Xinjiang, Sichuan, Yunnan, and Tibet .

HistoryIn 1958, Hay and Haynes first reported the complete synthesis of bergenin, using 4-methoxy gallate and A-D-bromo-2, 3, 4, 6-tetraacetylglucose as raw materials to synthesize bergenin successfully .In 1987, Chen Wendou determined the content of bergenin as 5.8% in the alcohol extract of Astilbe chinensis (Maxim.), Franch. et Savat.(Luoxinfu), and Rock cabbage (Bergenia purpurascens) by using high-performance liquid chromatography. In 1991, Wang Junping determined the content of bergenin in the alcohol extract of Rodgersia podophylla as 19.17% with spectrophotometry.By doing thin layer qualitative analysis, Liu Nunian discovered that bergenin could be found in seven kinds of plants including sour moss (Ardisia solanacea), Luosan tree (Ardisia quinquegona Bl.), Cinnabar root (Ardisia crenata Sims), Zijinniu (Ardisia japonica), Lianzuozijinniu (Ardisia primulaefolia), Jiujielong (Ardisia pusilla), and Xinyezijinniu (Ardisia maclurei) from Ardisia. In addition, Zhang Yi determined the content of bergenin in the medicinal plants from Ardisiawith high-performance liquid chromatography, and results showed that there were four species of plants with the content of bergenin of more than 1%, having great resource utilization value. There are 11 species of plants with the content of bergenin less than 1%, such as Xiaoqiaomuzijinniu (Ardisia arborescens), twist fruit, fine umbrella (Ardisia affinis Hemsl.), and so on. They had some useful value as well .In recent years, it has been found that both 8, 10-dimethylca bergenin and 11-0-gallate betaine had weak inhibitory effects on the tumor in mice, and their effects were stronger than that of bergenin. The effect of acetylated bergenin was stronger than that of bergenin on liver injury induced by chloroform in mice. The new bergenin derivatives from the Ardisia gigantifolia stapf had a certain degree of free radical-scavenging effect and anti-HIV viral activity .

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
InChIKey
YWJXCIXBAKGUKZ-HJJNZUOJSA-N
SMILES
O1[C@@H]2[C@H](OC(=O)c3c2c(c(c(c3)O)OC)O)[C@H]([C@@H]([C@H]1CO)O)O
LogP
-1.398 · -1.398 (est)
CAS DataBase Reference
477 · 477-90-7(CAS DataBase Reference)
FDA UNII
84 RBE4IDC · L84RBE4IDC
UNSPSC Code
85151701 · 85151701
NACRES
25 · NA.25
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-20/21/22
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
337200 · UQ0337200
HS Code
29329990 · 29329990
Storage Class
11 · 11 - Combustible Solids

UsesA herbal remedy with antioxidant, antimicrobial and antiinflammatory properties.

General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Upstream & downstream products

Upstream raw materials

Ethanol solution

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
桂林莱科生物科技有限公司18978670903 18107731009 · [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]
天津万象恒远科技有限公司15722085254 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [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]
上海思域化工科技有限公司86-21-34053660 · [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]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
苏州润新生物科技有限公司0512-62956991 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [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]
HBCChem, Inc.+1-510-219-6317 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
武汉励合化学新材料有限公司027-88395709
南京多隆生物科技有限公司18905173768 · [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]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
湖北康恩化学有限公司180-64105258 18064105258 · [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]
EMMX Biotechnology LLC888-539-0666 · [email protected]

Additional notes

DefinitionChEBI: A natural product found in Cenostigma gardnerianum.