Neohesperidin dihydrochalcone - ≥95% , CAS No.20702-77-6

CAS: 20702-77-6 Cat. No.: N140621 Molecular Weight: 612.58 EC Number: 243-978-6

GRADE & PURITY ≥95%

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-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

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

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504753412
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504753412
• Canonical 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
• 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
• InChIKey: ITVGXXMINPYUHD-CUVHLRMHSA-N
• 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
• 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=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides

• 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.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

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Homo sapiens (32628 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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TAS1R3 Tbio T1R1/T1R3 (473 Activities)

Discover Target: TAS1R3

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Associated Targets(non-human)

Cruzipain (33337 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Mechanisms of Action

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

References

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,      [PMID:38144792] [10.1016/j.fochx.2023.101023]

2. Caiying Zhang, Yuelong Li, Abdus Samad, Hongliang He, Huan Ma, Yang Chen, Tengchuan Jin.  (2023)  Kyasanur Forest disease virus NS3 helicase: Insights into structure, activity, and inhibitors.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:37924898] [10.1016/j.ijbiomac.2023.127856]

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,      [PMID:] [10.1016/j.jfca.2023.105584]

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,      [PMID:34224966] [10.1016/j.jchromb.2021.122767]

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,      [PMID:26453923] [10.1016/j.freeradbiomed.2015.08.023]

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,      [PMID:26362205] [10.1016/j.intimp.2015.09.003]

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,      [PMID:25978654] [10.1021/acs.jafc.5b01750]

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).  [PMID:] [10.1039/C4AY02004A]

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,      [PMID:] [10.1016/j.molstruc.2024.138416]

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,      [PMID:38317352] [10.1021/acs.jafc.3c08339]

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).  [PMID:38955844] [10.1007/s00604-024-06525-8]

12. Kuan Gao, Qin Geng, Changbao Hu, Wenhui Zhang, Xin Li, Ping Tong, Anshu Yang, Zhihua Wu, Hongbing Chen.  (2025)  Impact of the Polyphenol Structure on the Allergenic Potential of the Peanut Allergen Ara h 2.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:40586437] [10.1021/acs.jafc.5c05337]

13. Ruijie Xu, Xingyao Li, Xiaolun Peng, Junhui Xu, Yazhen Wang.  (2025)  Preparation of Al-MOF with different ligands for efficient electrochemical determination of neohesperidin dihydrochalcone (NHDC) in mud films.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2025.139190]

14. Xiaolun Peng, Ruijie Xu, Liang Zhang, Xingyao Li, Junhui Xu, Dongyun Huang, Yazhen Wang.  (2026)  Construction of multi-component CuO/ZIF-8@CNTs modified electrode for sensitive electrochemical detection of neohesperidin dihydrochalcone in liquor samples.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2026.108987]