Liquiritin

Liquiritin
Names
	IUPAC name (2S)-4′-(β-D-Glucopyranosyloxy)-7-hydroxyflavan-4-one
	Preferred IUPAC name (2S)-7-Hydroxy-4-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-4H-1-benzopyran-4-one
	Other names Liquiritoside; Liquiritigenin-4'-O-glucoside
Identifiers
CAS Number	551-15-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:80845 ;
ChemSpider	439855;
PubChem CID	503737;
UNII	T0O79T74CD ;
CompTox Dashboard (EPA)	DTXSID40203619 ;
	InChI InChI=1S/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1 Key: DEMKZLAVQYISIA-ZRWXNEIDSA-N; InChI=1/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1 Key: DEMKZLAVQYISIA-ZRWXNEIDBX;
	SMILES C1[C@H](OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O;
Properties
Chemical formula	C21H22O9
Molar mass	418.398 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Liquiritin is the 4'-O-glucoside of the flavanone liquiritigenin. Liquiritin is one of flavone compounds derived from licorice.^[1]

De novo biosynthesis of liquiritin in Saccharomyces cerevisiae using endogenous yeast metabolites as precursors and cofactors, provides a possibility for the economical and sustainable production and application of licorice flavonoids through synthetic biology.^[2]

References[]

^ Cong JX, Wang SY, Wu XH, Yu P (2012). "Optimization of Separation Conditions of Liquiritin in Preparative Liquid Chromatography". Advanced Materials Research. 550–553: 1647–1652. doi:10.4028/www.scientific.net/AMR.550-553.1647. S2CID 97214921.
^ Yin Y, Li Y, Jiang D, Zhang X, Gao W, Liu C (April 2020). "De novo biosynthesis of liquiritin in Saccharomyces cerevisiae". Acta Pharmaceutica Sinica B. 10 (4): 711–721. doi:10.1016/j.apsb.2019.07.005. PMC 7161706. PMID 32322472.

External links[]

Media related to Liquiritin at Wikimedia Commons

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[1] Cong JX, Wang SY, Wu XH, Yu P (2012). "Optimization of Separation Conditions of Liquiritin in Preparative Liquid Chromatography". Advanced Materials Research. 550–553: 1647–1652. doi:10.4028/www.scientific.net/AMR.550-553.1647. S2CID 97214921.

[pmid32322472-2] Yin Y, Li Y, Jiang D, Zhang X, Gao W, Liu C (April 2020). "De novo biosynthesis of liquiritin in Saccharomyces cerevisiae". Acta Pharmaceutica Sinica B. 10 (4): 711–721. doi:10.1016/j.apsb.2019.07.005. PMC 7161706. PMID 32322472.

[1]

[2]

v t Flavanones and their glycosides
Flavanones	Butin Eriodictyol Naringenin Pinocembrin
O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin (Pinocembrin-7-methylether) Sakuranetin Sterubin
C-methylated flavanones	Poriol
Glycosides	Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin
Acetylated	8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G
Acetylated glycosides

v t Glycosides
Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond
Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside
Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside
Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

Names

IUPAC name (2S)-4′-(β-D-Glucopyranosyloxy)-7-hydroxyflavan-4-one
Preferred IUPAC name (2S)-7-Hydroxy-4-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names Liquiritoside Liquiritigenin-4'-O-glucoside
Identifiers
CAS Number	551-15-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:80845^Y
ChemSpider	439855
PubChem CID	503737
UNII	T0O79T74CD^Y
CompTox Dashboard (EPA)	DTXSID40203619
InChI InChI=1S/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1 Key: DEMKZLAVQYISIA-ZRWXNEIDSA-N InChI=1/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1 Key: DEMKZLAVQYISIA-ZRWXNEIDBX
SMILES C1[C@H](OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
Properties
Chemical formula	C₂₁H₂₂O₉
Molar mass	418.398 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Liquiritin

References[]

Further reading[]

External links[]