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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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Properties

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Impact of Gelatin Supplemented with Gum Arabic, Tween 20, and β-Cyclodextrin on the Microencapsulation of Turkish Oregano Extract.

Juste Baranauskaite et al.

Molecules (Basel, Switzerland), 24(1) (2019-01-10)

Microencapsulation protects core materials from deteriorating due to environmental conditions, such as moisture or oxidation, and improves the bioavailability of active compounds, allowing one to make solid formulations from oils and increase their solubility. Wall and core material properties determine

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

Formation and Investigation of Electrospun Eudragit E100/Oregano Mats.