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Neohesperidin dihydrochalcone - ≥95%, high purity , CAS No.20702-77-6
Basic Description
Synonyms
3,5-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside | 1-(4-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-
Specifications & Purity
≥95%
Storage Temp
Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Phenylpropanoids and polyketides
Class
Flavonoids
Subclass
Flavonoid glycosides
Intermediate Tree Nodes
Not available
Direct Parent
Flavonoid O-glycosides
Alternative Parents
2'-Hydroxy-dihydrochalcones Cinnamylphenols Phenolic glycosides Alkyl-phenylketones Butyrophenones Disaccharides O-glycosyl compounds Methoxyphenols Anisoles Aryl alkyl ketones Benzoyl derivatives Resorcinols Methoxybenzenes Phenoxy compounds 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Oxanes Vinylogous acids Secondary alcohols Polyols Acetals Oxacyclic compounds Primary alcohols Hydrocarbon derivatives Organic oxides
Molecular Framework
Aromatic heteromonocyclic compounds
Substituents
Flavonoid o-glycoside - 2'-hydroxy-dihydrochalcone - Phenolic glycoside - Linear 1,3-diarylpropanoid - Cinnamylphenol - Alkyl-phenylketone - Butyrophenone - Disaccharide - Glycosyl compound - O-glycosyl compound - Methoxyphenol - Phenylketone - Anisole - Benzoyl - Phenoxy compound - Phenol ether - Resorcinol - Methoxybenzene - Aryl ketone - Aryl alkyl ketone - Alkyl aryl ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Oxane - Vinylogous acid - Ketone - Secondary alcohol - Polyol - Ether - Oxacycle - Organoheterocyclic compound - Acetal - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Primary alcohol - Organooxygen compound - Alcohol - Aromatic heteromonocyclic compound
Description
This compound belongs to the class of organic compounds known as flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
External Descriptors
disaccharide derivative - dihydrochalcones - neohesperidoside
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
Pubchem Sid
504753412
Pubchem Sid Url
https://pubchem.ncbi.nlm.nih.gov/substance/504753412
IUPAC Name
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
INCHI
InChI=1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
InChIKey
ITVGXXMINPYUHD-CUVHLRMHSA-N
Smiles
CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC(=C(C=C4)OC)O)O)CO)O)O)O)O)O
Isomeric SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC(=C(C=C4)OC)O)O)CO)O)O)O)O)O
WGK Germany
3
RTECS
LZ5785000
Molecular Weight
612.58
Reaxy-Rn
25642580
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25642580&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Melt Point(°C)
156-158°C
Molecular Weight
612.600 g/mol
XLogP3
-0.300
Hydrogen Bond Donor Count
9
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
10
Exact Mass
612.205 Da
Monoisotopic Mass
612.205 Da
Topological Polar Surface Area
245.000 Ų
Heavy Atom Count
43
Formal Charge
0
Complexity
882.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
10
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Chengyun He, Lu Bai, Daqun Liu, Benguo Liu.
(2023)
Interaction mechanism of okra (Abelmoschus esculentus L.) seed protein and flavonoids: Fluorescent and 3D-QSAR studies. Food Chemistry-X,
20
(101023).
2.
Caiying Zhang, Yuelong Li, Abdus Samad, Hongliang He, Huan Ma, Yang Chen, Tengchuan Jin.
(2024)
Kyasanur Forest disease virus NS3 helicase: Insights into structure, activity, and inhibitors. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,
254
(127856).
3.
Liang Zhang, Junhui Xu, Jing Qian, Yazhen Wang.
(2023)
A novel detection method for neohesperidin dihydrochalcone (NHDC) based on ZIF-8/ErGO composite modified electrode in milk. JOURNAL OF FOOD COMPOSITION AND ANALYSIS,
123
(105584).
4.
Zilong Chen, Hongdong Liu, Jie Chen, Weifeng Zhu, Yong Liu, Jianxin Min, Xiaotian Chen, Bin Li, Xin Yang.
(2021)
Separation and enrichment of sibiskoside from Sibiraea angustat with magnetic surface dummy template molecularly imprinted polymers. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,
1178
(122767).
5.
Xiaomin Xia, Juanli Fu, Xiufang Song, Qiong Shi, Chuanyang Su, Erqun Song, Yang Song.
(2015)
Neohesperidin dihydrochalcone down-regulates MyD88-dependent and -independent signaling by inhibiting endotoxin-induced trafficking of TLR4 to lipid rafts. FREE RADICAL BIOLOGY AND MEDICINE,
89
(522).
6.
Qiong Shi, Xiufang Song, Juanli Fu, Chuanyang Su, Xiaomin Xia, Erqun Song, Yang Song.
(2015)
Artificial sweetener neohesperidin dihydrochalcone showed antioxidative, anti-inflammatory and anti-apoptosis effects against paraquat-induced liver injury in mice. INTERNATIONAL IMMUNOPHARMACOLOGY,
29
(722).
7.
Chuanyang Su, Xiaomin Xia, Qiong Shi, Xiufang Song, Juanli Fu, Congxue Xiao, Hongjun Chen, Bin Lu, Zhiyin Sun, Shanmei Wu, Siyu Yang, Xuegang Li, Xiaoli Ye, Erqun Song, Yang Song.
(2015)
Neohesperidin Dihydrochalcone versus CCl4-Induced Hepatic Injury through Different Mechanisms: The Implication of Free Radical Scavenging and Nrf2 Activation. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,
63
(22):
(5468–5475).
8.
Lingxi Yang, Lu Wang, Kunjing Li, Baoxian Ye.
(2014)
Sensitive voltammetric determination of neohesperidin dihydrochalcone based on SWNTs modified glassy carbon electrode. Analytical Methods,
6
(23):
(9410-9418).
9.
Mengyao Jiang, Yu Yan, Chuanying Zhang, Haibing Liao, Mengfan Wang, Xin Peng.
(2024)
Investigation on the binding behaviors of two dihydrochalcones to bovine serum albumin and their anti-glycation activities. JOURNAL OF MOLECULAR STRUCTURE,
1311
(138416).
10.
Yucong Zou, Xiaofeng Li, Xuan Xin, Haixia Xu, Guanglei Zhao.
(2024)
Microbial-Driven Synthesis and Hydrolysis of Neohesperidin Dihydrochalcone: Biotransformation Process and Feasibility Investigation. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,
72
(8):
(4246-4256).
11.
Xu Ruijie, Liu Zhenkang, Kong Zhibo, Ma Xinyu, Peng Xiaolun, Wang Yazhen.
(2024)
Preparation of CoFe@C composite modified electrode for neohesperidin dihydrochalcone sensing and its application in Chinese medicine. MICROCHIMICA ACTA,
191
(8):
(1-13).
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11 Citations
H2125020