Glabridin - 10mM in DMSO , CAS No.59870-68-7

CAS: 59870-68-7 Cat. No.: G424980 Molecular Weight: 324.37 EC Number: 611-908-7

GRADE & PURITY 10mM in DMSO

Synonyms

HMS3885M04 | BCP29437 | CHEBI:5369 | GLABRIDIN [INCI] | 1,3-BENZENEDIOL, 4-((3R)-3,4-DIHYDRO-8,8-DIMETHYL-2H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-3-YL)- | 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl]benzene-1,3-diol | MLS000697609 | LM

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

HMS3885M04 | BCP29437 | CHEBI:5369 | GLABRIDIN [INCI] | 1, 3-BENZENEDIOL, 4-((3R)-3, 4-DIHYDRO-8, 8-DIMETHYL-2H, 8H-BENZO(1, 2-B:3, 4-B')DIPYRAN-3-YL)- | 4-[(3R)-8, 8-dimethyl-3, 4-dihydro-2H, 8H-benzo[1, 2-b:3, 4-b']dipyran-3-yl]benzene-1, 3-diol | MLS000697609 | LM

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Antiproliferative agent. Inhibits melanogenesis. Induces apoptosis through caspase 3, 8, and 9 activation and PARP cleavage. Activates ERK1/2, p38 MAPK and JNK1/2. Shows estrogenic, neuroprotective, depigmenting and antitumor effects in vivo.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: CC1(C=CC2=C(O1)C=CC3=C2OCC(C3)C4=C(C=C(C=C4)O)O)C
• IUPAC Name: 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
• InChIKey: LBQIJVLKGVZRIW-ZDUSSCGKSA-N
• INCHI: 1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1
• Isomeric SMILES: CC1(C=CC2=C(O1)C=CC3=C2OC[C@H](C3)C4=C(C=C(C=C4)O)O)C
• Molecular Weight: 324.37
• Reaxy-Rn: 5982641
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5982641&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Isoflavonoids
      • Subclass Pyranoisoflavonoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Isoflavonoids
• Subclass: Pyranoisoflavonoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyranoisoflavonoids
• Alternative Parents: Isoflavanols Hydroxyisoflavonoids Pyranochromenes 2,2-dimethyl-1-benzopyrans Resorcinols Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Oxacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyranoisoflavonoid - Hydroxyisoflavonoid - Isoflavanol - Isoflavan - Pyranochromene - 2,2-dimethyl-1-benzopyran - Chromane - Benzopyran - 1-benzopyran - Resorcinol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Oxacycle - Organoheterocyclic compound - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.
• External Descriptors: Isoflavans

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)

TYR Tclin Tyrosinase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TYR Tclin Tyrosinase (717 Activities)

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CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)

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PON1 Tbio Serum paraoxonase/arylesterase 1 (96 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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CYP2B6 Tchem Cytochrome P450 2B6 (1338 Activities)

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MCF7 (126967 Activities)

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SW480 (6023 Activities)

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A549 (127892 Activities)

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HepG2 (196354 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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BRCA1 Tchem Breast cancer type 1 susceptibility protein (15908 Activities)

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SNCA Tchem Alpha-synuclein (10960 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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GMNN Tbio Geminin (128009 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

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HEK-293T (167025 Activities)

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L02 (4864 Activities)

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Associated Targets(non-human)

Ttr Transthyretin (14 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Salmonella enterica subsp. enterica serovar Gallinarum (105 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Pichia kudriavzevii (7448 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Nakaseomyces glabratus (9108 Activities)

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Candida parapsilosis (8521 Activities)

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Candida tropicalis (8381 Activities)

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Mus musculus (284745 Activities)

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RAW264.7 (28094 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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HSP40, subfamily A, putative (505 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 156-158°C
• Molecular Weight: 324.400 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 324.136 Da
• Monoisotopic Mass: 324.136 Da
• Topological Polar Surface Area: 58.900 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 488.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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. Chunxing Pan, Xiaoying Liu, Yating Zheng, Zejun Zhang, Yongliang Li, Biao Che, Guangrong Liu, Lanyue Zhang, Changzhi Dong, Haji Akber Aisa, Zhiyun Du, Zhengqiang Yuan.  (2022)  The mechanisms of melanogenesis inhibition by glabridin: molecular docking, PKA/MITF and MAPK/MITF pathways.  Food Science and Human Wellness,      [PMID:] [10.1016/j.fshw.2022.07.011]

2. Lu Wang, Qiong Liu, Baoxian Ye.  (2020)  An electroanalytical method for glabridin investigation based on poly(diallyldimethylammonium chloride)-functionalized graphene-modified electrode.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2020.105279]

3. Mei-yuan Li, Zhi-peng Jia, De-min Li, Man-ping Luo, Ying-ying Meng, Kang- xu Wang, Bei Wang, Bing Liu, Xin-guo Zhang, Qin Li.  (2024)  Enhanced co-extraction of glycyrrhizic acid and glabridin from Glycyrrhiza glabra L. through enzyme-focused techniques.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2024.118145]

4. Weng Jiyu, Wang Ying, Tan Zekai, Yuan Yanghe, Huang Shiyuan, Li Zexi, Li Yiming, Zhang Lanyue, Du Zhiyun.  (2024)  Glabridin reduces neuroinflammation by modulating inflammatory signals in LPS-induced in vitro and in vivo models.  INFLAMMOPHARMACOLOGY,      [PMID:38372849] [10.1007/s10787-023-01424-5]

5. Yuyang Cao, Duoling Xu, Zhaoji Zu, Genlu Xu, Yixi Zeng, Jiyu Weng, Zhenhai Huang, Hongping Xiang, Lanyue Zhang, Jinlong Ding, Hui Li.  (2024)  Thermosensitive, injectable, antibacterial glabridin liposome/chitosan dual network hydrogel for diabetic wound healing.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39708855] [10.1016/j.ijbiomac.2024.138966]

6. Lili Li, Xiaoya Zhang, Guangyuan Tang, Jianxin Wu, Qing Huang.  (2026)  Glabridin Inhibits Melanogenesis and Melanin Transfer via Wnt/β-Catenin Pathway and Rho Family GTPase-Mediated Dendritic Formation Suppression.  Pharmaceuticals,  19  (3): (469).  [PMID:41901315] [10.3390/ph19030469]