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R4033

Sigma-Aldrich

Rosmarinic acid

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

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C18H16O8
Número de CAS:
20283-92-5
Peso molecular:
360.31
Beilstein:
2227587
Número MDL:
MFCD00017740
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
329824027
NACRES:
NA.25

origen biológico

Rosemarinus officinalis L.

Ensayo

≥98% (HPLC)

Formulario

powder

condiciones de almacenamiento

protect from light

color

white to faint beige

mp

171-175 °C (lit.)

solubilidad

H2O: 1 mg/mL, clear, colorless

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

DOUMFZQKYFQNTF-WUTVXBCWSA-N

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Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
BCCG5554
BCCF4141
BCCC1241
BCBZ7196
BCBV7877

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05330590

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Caffeic acid ≥98.0% (HPLC)

Sigma-Aldrich

C0625

Caffeic acid

Carnosol phyproof® Reference Substance

PHL80150

Carnosol

USP

USP

1605668

Powdered Rosemary Extract

Salvianolic acid B ≥94% (HPLC)

Sigma-Aldrich

SML0048

Salvianolic acid B

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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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