Rhododendrin

Rhododendrin
Names
	IUPAC name (2R)-4-(4-Hydroxyphenyl)butan-2-yl β-D-glucopyranoside
	Systematic IUPAC name (2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-{[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxy}oxane-3,4,5-triol
	Other names Betuloside; (-)-Rhododendrin
Identifiers
CAS Number	497-78-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1086682;
ChemSpider	390960;
PubChem CID	442538;
UNII	5I7QR8C454 ;
	InChI InChI=1S/C16H24O7/c1-9(2-3-10-4-6-11(18)7-5-10)22-16-15(21)14(20)13(19)12(8-17)23-16/h4-7,9,12-21H,2-3,8H2,1H3/t9-,12-,13-,14+,15-,16-/m1/s1 Key: KLLYDTMVSVIJEH-YYMOATHLSA-N;
	SMILES CC(CCC1=CC=C(C=C1)O)OC2C(C(C(C(O2)CO)O)O)O;
Properties
Chemical formula	C16H24O7
Molar mass	328.361 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

Rhododendrin (betuloside) is an arylbutanoid glycoside and a phenylpropanoid, a type of natural phenol. It can be found in the leaves of Rhododendron aureum^[1] or in Cistus salviifolius.^[2]

In vitro, it shows analgesic, anti-inflammatory^[1] and diuretic^[3] properties.

References

↑ ^1.0 ^1.1 Kim, M. H.; Nugroho, A.; Choi, J.; Park, J. H.; Park, H. J. (2011). "Rhododendrin, an analgesic/anti-inflammatory arylbutanoid glycoside, from the leaves of Rhododendron aureum". Archives of Pharmacal Research 34 (6): 971–978. doi:10.1007/s12272-011-0614-1. PMID 21725818.
↑ Danne, A.; Petereit, F.; Nahrstedt, A. (1994). "Flavan-3-ols, prodelphinidins and further polyphenols from Cistus salvifolius". Phytochemistry 37 (2): 533–538. doi:10.1016/0031-9422(94)85094-1. PMID 7765630.
↑ Zhang, B; Li, JB; Zhang, DM; Ding, Y; Du, GH (2007). "Analgesic and anti- inflammatory activities of a fraction rich in gaultherin isolated from Gaultheria yunnanensis (Franch.)". Pharmacognosy Reviews 30 (10): 465–469. doi:10.4103/0973-7847.91102. PMID 22279370.

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[KimMH-1] 1.0 ^1.1 Kim, M. H.; Nugroho, A.; Choi, J.; Park, J. H.; Park, H. J. (2011). "Rhododendrin, an analgesic/anti-inflammatory arylbutanoid glycoside, from the leaves of Rhododendron aureum". Archives of Pharmacal Research 34 (6): 971–978. doi:10.1007/s12272-011-0614-1. PMID 21725818.

[2] Danne, A.; Petereit, F.; Nahrstedt, A. (1994). "Flavan-3-ols, prodelphinidins and further polyphenols from Cistus salvifolius". Phytochemistry 37 (2): 533–538. doi:10.1016/0031-9422(94)85094-1. PMID 7765630.

[Zhang-3] Zhang, B; Li, JB; Zhang, DM; Ding, Y; Du, GH (2007). "Analgesic and anti- inflammatory activities of a fraction rich in gaultherin isolated from Gaultheria yunnanensis (Franch.)". Pharmacognosy Reviews 30 (10): 465–469. doi:10.4103/0973-7847.91102. PMID 22279370.

[1]

[2]

[3]

v t e Types of phenylpropanoids
Classes of phenylpropanoids	Hydroxycinnamic acids Chromones (Furanochromones) Cinnamaldehydes Monolignols Coumarins Chalcones Flavonoids Phenylpropenes Stilbenoids Lignans Lignins Suberins
Examples	Rhododendrin

Names

IUPAC name (2R)-4-(4-Hydroxyphenyl)butan-2-yl β-D-glucopyranoside
Systematic IUPAC name (2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-{[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxy}oxane-3,4,5-triol
Other names Betuloside (-)-Rhododendrin
Identifiers
CAS Number	497-78-9^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1086682
ChemSpider	390960
PubChem CID	442538
UNII	5I7QR8C454^Y
InChI InChI=1S/C16H24O7/c1-9(2-3-10-4-6-11(18)7-5-10)22-16-15(21)14(20)13(19)12(8-17)23-16/h4-7,9,12-21H,2-3,8H2,1H3/t9-,12-,13-,14+,15-,16-/m1/s1 Key: KLLYDTMVSVIJEH-YYMOATHLSA-N
SMILES CC(CCC1=CC=C(C=C1)O)OC2C(C(C(C(O2)CO)O)O)O
Properties
Chemical formula	C₁₆H₂₄O₇
Molar mass	328.361 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

Rhododendrin

Topic: Chemistry

References