All Photos(1)

536954

Sigma-Aldrich

Rosmarinic acid

96%

Synonym(s):
3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester, (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid
Empirical Formula (Hill Notation):
C18H16O8
CAS Number:
Molecular Weight:
360.31
Beilstein:
2227587
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

form

powder

mp

171-175 °C (lit.)

SMILES string

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

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

InChI key

DOUMFZQKYFQNTF-WUTVXBCWSA-N

Gene Information

human ... LCK(3932)

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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.

Packaging

5 g in glass bottle

Biochem/physiol Actions

Rosmarinic acid has shown to contain antioxidant, anti-inflammatory and antimicrobial activities. Possesses promising physiological actions related to cognitive performance, Alzheimer′s disease prevention, kideney disease treatment, cardioprotection and cancer chemoprevention.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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 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)
Effect of rosmarinic acid on inhibition of gentamicin induced nephrotoxicity in rats.
Tavafi M and Ahmadvand H
Tissue & cell, 43(6), 392-397 (2011)
Vivek Swarup et al.
Antimicrobial agents and chemotherapy, 51(9), 3367-3370 (2007-06-20)
Rosmarinic acid (RA) reduced the mortality of mice infected with Japanese encephalitis virus (JEV). Significant decreases in viral loads (P < 0.001) and proinflammatory cytokine levels (P < 0.001) were observed in JEV-infected animals treated with RA compared to levels
Mélanie Dubois et al.
Journal of medicinal chemistry, 51(8), 2575-2579 (2008-03-21)
Rosmarinic acid was reacted with nitrite ions under acidic conditions to give 6'-nitro- and 6',6''-dinitrorosmarinic acids according to the reaction time. Both compounds were active as HIV-1 integrase inhibitors at the submicromolar level. They also inhibited the viral replication in

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