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R4033

Sigma-Aldrich

Rosmarinic acid

≥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
Beilstein:
2227587
MDL number:
MFCD00017740
UNSPSC Code:
12352106
PubChem Substance ID:
329824027
NACRES:
NA.25

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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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Juste Baranauskaite et al.
Molecules (Basel, Switzerland), 24(3) (2019-02-14)
An electrospun mat of Eudragit E100 (EE100) (a cationic copolymer based on dimethylaminoethyl methacrylate, butyl methacrylate, and methyl methacrylate) was used as a delivery system for oregano ethanolic extract (OEE). Oregano is a biologically active material which is widely used
Robert Domitrović et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 51, 370-378 (2012-11-03)
The aim of this study was to investigate the therapeutic potential of rosmarinic acid (RA), a natural phenolic, in the treatment of acute liver toxicity. RA at 10, 25 and 50mg/kg was administered by gavage once daily for 2 consecutive
Cristina Airoldi et al.
Chemistry, an Asian journal, 8(3), 596-602 (2013-01-11)
Amyloid peptides, Aβ1-40 and Aβ1-42, represent major molecular targets to develop potential drugs and diagnostic tools for Alzheimer's Disease (AD). In fact, oligomeric and fibrillar aggregates generated by these peptides are amongst the principal components of amyloid plaques found post
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