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

Tracking categories (test):

* SizeSet

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. ↑ 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.
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.

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Types of phenylpropanoids

Classes of phenylpropanoids|

* Hydroxycinnamic acids
* Chromones (Furanochromones)
* Cinnamaldehydes
* Monolignols
* Coumarins
* Chalcones
* Flavonoids
* Phenylpropenes
* Stilbenoids
* Lignans
* Lignins
* Suberins

Examples|

* Rhododendrin

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