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Robinin
Robinin structure
Robinin structure
Names
IUPAC name
4′,5-Dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranosyloxy]-7-(α-L-rhamnopyranosyloxy)flavone
Systematic IUPAC name
(12S,13R,14R,15R,16S,52S,53R,54S,55R,56R,82R,83R,84R,85R,86S)-13,14,15,35,53,54,55,83,84,85-Decahydroxy-32-(4-hydroxyphenyl)-16,86-dimethyl-34H-2,4,7-trioxa-3(7,3)-[1]benzopyrana-1,8(2),5(2,6)-tris(oxana)octaphan-34-one
Other names
Kaempferol-3-O-gal-rham-7-O-rham
Kaempferol-3-O-robinoside-7-O-rhamnoside
Kaempferol robinoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.559 Edit this at Wikidata
EC Number
  • 206-113-3
KEGG
UNII
  • InChI=1S/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,28+,31+,32-,33-/m0/s1 ☒N
    Key: PEFASEPMJYRQBW-HKWQTAEVSA-N ☒N
  • InChI=1/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,28+,31+,32-,33-/m0/s1
    Key: PEFASEPMJYRQBW-HKWQTAEVBB
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)O)O)O)C6=CC=C(C=C6)O)O)O)O)O)O)O
Properties
C33H40O19
Molar mass 740.66 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Robinin (IUPAC: kaempferol-3-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranoside-7-O-(6-deoxy-α-L-mannopyranosyl)oxy) is a naturally occurring flavonoid glycoside, classified as a flavonol O-glycoside.[1] or from the common locust Robinia pseudoacacia.[2] It is chemically derived as a flavone glycoside from the aglycone Kaempferol, and occurs naturally in several plant species.[3]

Robinin is found in plants of the family Fabaceae, particularly in the genus Robinia, such as Robinia pseudoacacia (black locust or robinia). It has also been reported in other genera, including Vigna and Pueraria.[4]

Chemical properties

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Robinin has the molecular formula C33H40O19 and a molecular weight of 740.66 g/mol.[5]

It is a diglycoside of kaempferol, with sugar moieties attached at the -3 and -7 positions of the flavonol skeleton. These sugars include rhamnose and galactose residues linked through glycosidic bonds.[6]

Biological activities and applications

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Preliminary research suggests that robinin exhibits anti-inflammatory, antibacterial, and cardioprotective properties.[7] It has been reported to inhibit the TLR4/NF-κB signaling pathway in human peripheral blood mononuclear cells and to reduce cardiotoxicity in animal models.

While robinin has demonstrated bioactivity in laboratory studies, it currently has no approved therapeutic or pharmacological use in humans.[8]

See also

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References

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  1. ^ Akhmedzhanova, V. (1986). "Robinin and kaempfereol fromVinca erecta". Chemistry of Natural Compounds. 22 (5): 601–602. Bibcode:1986CNatC..22..601A. doi:10.1007/BF00599275. S2CID 4827681.
  2. ^ Sando, Charles E. (1932). "The Plant Coloring Matter, Robinin". Journal of Biological Chemistry. 94 (3): 675–680. doi:10.1016/s0021-9258(18)76392-8.
  3. ^ "Robinin - ChemicalBook". ChemicalBook. Retrieved 30 October 2025.
  4. ^ "Robinin - Product Data". ChemicalBook. Retrieved 30 October 2025.
  5. ^ "Robinin - Chemical Properties". ChemicalBook. Retrieved 30 October 2025.
  6. ^ "Robinin - PubChem". PubChem. Retrieved 30 October 2025.
  7. ^ "Robinin - GLPBio Product Information". GLPBio. Retrieved 30 October 2025.
  8. ^ "Natural Flavonoids and Polyphenols Review". MDPI International Journal of Molecular Sciences. Retrieved 30 October 2025.
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