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Merck
CN

536954

Rosmarinic acid

96%

Synonym(s):

(R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid, 3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C18H16O8
CAS Number:
20283-92-5
Molecular Weight:
360.31
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
24878185
MDL number:
MFCD00017740
Beilstein/REAXYS Number:
2227587
Assay:
96%
Form:
powder

Key Documents

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form

powder

InChI

1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1

SMILES string

OC(=O)[C@@H](Cc1ccc(O)c(O)c1)OC(=O)\C=C\c2ccc(O)c(O)c2

InChI key

DOUMFZQKYFQNTF-WUTVXBCWSA-N

assay

96%

Quality Level

200

Gene Information

human ... LCK(3932)

mp

171-175 °C (lit.)

functional group

carboxylic acid, ester

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General description

Rosmarinic acid is a bioactive plant phenolic compound with antioxidant and anti-inflammatory effects.

Application

Rosmarinic acid has been used as a model compound to study its biological effects in animal models. Various studies have shown its ability to:
  • Inhibit nephropathy.
  • Inhibit gentamicin sulfate (GS)-induced renal oxidative damage.
  • Reduce noise-induced hearing loss.
  • Reduce depression.
  • Reduce post-traumatic stress disorder (PTSD)-like symptoms.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000496471
0000496471
BCCN7989
0000459179
0000459179

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Daseul Kim et al.
Pharmaceutics, 11(7) (2019-06-30)
Amongst various drug administration methods, ophthalmic drug delivery has been a useful way for the treatment of eye-related diseases. However, therapeutic efficacy of ocular therapy for anterior or posterior eye segments through topical administration is considerably challenged by the number
Rosmarinic acid ameliorates PTSD-like symptoms in a rat model and promotes cell proliferation in the hippocampus.
Nie H, et al.
Progress in Neuro-Psychopharmacology & Biological Psychiatry, 51, 16-22 (2014)
Rosmarinic acid up-regulates the noise-activated Nrf2/HO-1 pathway and protects against noise-induced injury in rat cochlea.
Fetoni A R, et al.
Free Radical Biology & Medicine, 83, 269-281 (2015)
Rosmarinic acid ameliorates diabetic nephropathy in uninephrectomized diabetic rats.
Tavafi M, et al.
Iranian Journal of Basic Medical Sciences, 14(3), 275-275 (2011)
Effect of rosmarinic acid on inhibition of gentamicin induced nephrotoxicity in rats.
Tavafi M and Ahmadvand H
Tissue & cell, 43(6), 392-397 (2011)
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