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R4033

Rosmarinic acid

Name: Rosmarinic acid
Brand: SIGMA

≥98% (HPLC), from Rosemarinus officinalis L.

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.25

PubChem Substance ID:

329824027

MDL number:

MFCD00017740

Beilstein/REAXYS Number:

2227587

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biological source

Rosemarinus officinalis L.

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to faint beige

mp

171-175 °C (lit.)

solubility

H₂O: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

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

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Biochemicals

Natural Products for Research and Discovery

General description

Rosmarinic acid is a naturally occurring polyphenolic compound found in plants of the Boraginaceae family and Nepetoideae subfamily. It is an ester of caffeic acid as well as 3,4-dihydroxy-phenyllactic acid.

Application

Rosmarinic acid has been used:

to see its protective effects on the human endothelial cell line (EA.hy926) to treat diabetic atherosclerosis
to test its effect in 1-Methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) induced Parkinson′s disease (PD) models on attenuating inflammatory responses and microglia activation
to test its neuroprotective effects on dopaminergic neurons
to test its effects on sperm motility, viability and on intracellular calcium ion concentration
as a reference standard in capillary zone electrophoresis (CZE) method

Biochem/physiol Actions

Rosmarinic acid (RosA) is a well-appreciated agent used in several diabetic conditions and complications such as diabetic nephropathy, diabetic neuropathy and diabetic atherosclerosis. It has also been implicated to be a neuroprotective agent for several neurological disorders such as Alzheimer′s disease, Parkinson′s disease, and epilepsy by suppressing their conditions.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Rosmarinic acid compromises human sperm functions by an intracellular Ca2+ concentration-related mechanism.

Meng-Ge Lv et al.

Reproductive toxicology (Elmsford, N.Y.), 81, 58-63 (2018-07-17)

Rosmarinic acid (RA), a natural phenolic ester, is cytoprotective for male reproduction in animal models. The present study investigated the in vitro actions of RA on human sperm functions. Human sperm were exposed to 1, 10, 100, and 1000 μM

Investigation of antioxidant effects of rosmarinic acid on liver, lung and kidney in rats: a biochemical and histopathological study.

A Oğuz et al.

Folia morphologica, 79(2), 288-295 (2019-08-23)

The aim of the study was to investigate the protective effects of rosmarinic acid in rats exposed to hepatic ischaemia/reperfusion (I/R) injury. Thirty-two rats were randomly classified into four groups of 8 rats each: laparotomy without medication, rosmarinic acid (dose

Rosmarinic acid suppresses Alzheimer's disease development by reducing amyloid β aggregation by increasing monoamine secretion.

Tomoki Hase et al.

Scientific reports, 9(1), 8711-8711 (2019-06-20)

A new mechanism is revealed by which a polyphenol, rosmarinic acid (RA), suppresses amyloid β (Aβ) accumulation in mice. Here we examined the brains of mice (Alzheimer's disease model) using DNA microarray analysis and revealed that the dopamine (DA)-signaling pathway

Polyphenols analysis from different medicinal plants extracts using capillary zone electrophoresis (CZE)

Matei AO, et al.,

Revista de Chimie, 67, 1051-1105 (2016)

Barrier protective effects of rosmarinic acid on HMGB1-induced inflammatory responses in vitro and in vivo.

Eun-Ju Yang et al.

Journal of cellular physiology, 228(5), 975-982 (2012-10-09)

High mobility group box 1 (HMGB1) protein is a crucial cytokine that mediates response to infection, injury, and inflammation. Rosmarinic acid (RA) is an important component of the leaves of Perilla frutescens and has neuroprotective, anti-microbial, anti-oxidant, and anti-cancer effects

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Global Trade Item Number

SKU	GTIN
R4033-10MG	04061836695187
R4033-50MG	04061836695194

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