Rosmarinic acid

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Names

[ CAS No. ]:
20283-92-5

[ Name ]:
Rosmarinic acid

[Synonym ]:
R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acid
MFCD00017740
ROSMARINATE
(R)-rosmarinic acid
(+)-Rosmarinic acid
Benzenepropanoic acid, α-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxy-, (αR)-
Rosemary acid
(2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
(2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}propanoic acid
RosmarinicAcid
Rosmarinic acid
rosemaryacid
Rosmarinic
Rosemaricacid
Labiatenic acid
3,4-Dihydroxycinnamicacid(R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethylester
(R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4-dihydroxyphenyl)lacticacid
4-dihydroxy

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
694.7±55.0 °C at 760 mmHg

[ Melting Point ]:
171-175 °C(lit.)

[ Molecular Formula ]:
C18H16O8

[ Molecular Weight ]:
360.315

[ Flash Point ]:
254.5±25.0 °C

[ Exact Mass ]:
360.084503

[ PSA ]:
144.52000

[ LogP ]:
1.70

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.714

[ Storage condition ]:
Store at RT

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GD8990000
CHEMICAL NAME :
Cinnamic acid, 3,4-dihydroxy-, 2-ester with 3-(3,4-dihydroxyphenyl)lactic acid
CAS REGISTRY NUMBER :
20283-92-5
LAST UPDATED :
199409
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C18-H16-O8
MOLECULAR WEIGHT :
360.34

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
561 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 10,756,1985

Safety Information

[ Symbol ]:

GHS06, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H400

[ Precautionary Statements ]:
P273-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
GD8990000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • (R,E)-1-(allyloxy)-3-(3,4-dihydroxyphenyl)-1-oxopropan-2-yl 3-(3,4-dihydroxyphenyl)acrylate
  • (R)-1-(allyloxy)-3-(3,4-bis(allyloxy)phenyl)-1-oxopropan-2-yl (E)-3-(3,4-bis(allyloxy)phenyl)acrylate
  • (Z)-3-(3,4-dihydroxyphenyl)-2-hydroxyacrylic acid
  • Danshensu lactic acid
  • 3,4-diprop-2-enoxybenzaldehyde
  • 3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoic acid
  • (R,E)-1-(allyloxy)-3-(benzo[d][1,3]dioxol-5-yl)-1-oxopropan-2-yl 3-(3,4-bis(benzyloxy)phenyl)acrylate

DownStream

  • Caffeic acid
  • Danshensu lactic acid
  • DL-alpha-Tocopherol
  • methyl 3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enoate

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Methanolic extract of Origanum vulgare ameliorates type 1 diabetes through antioxidant, anti-inflammatory and anti-apoptotic activity.

Br. J. Nutr. 113(5) , 770-82, (2015)

Type 1 diabetes (T1D), an autoimmune inflammatory disorder, develops as a consequence of pancreatic β-cell destruction and results in hyperglycaemia. Since current T1D therapy mainly involves insulin ...

The hepatoprotection of caffeic acid and rosmarinic acid, major compounds of Perilla frutescens, against t-BHP-induced oxidative liver damage.

Food Chem. Toxicol. 55 , 92-9, (2013)

Perilla frutescens leaves are often used in East Asian gourmet food. In this study, we investigated the hepatoprotective effects of caffeic acid (CA), rosmarinic acid (RA), and their combination. P. f...

Investigating the potential of under-utilised plants from the Asteraceae family as a source of natural antimicrobial and antioxidant extracts.

Food Chem. 161 , 79-86, (2014)

Antimicrobial properties of ethanol and water extracts from eight Asteraceae species were investigated against three Gram positive (Staphylococcus aureus, MRSA and Bacillus cereus) and two Gram negati...


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Related Compounds

  • Rosmarinic acid
  • Inoveol rosmarinic acid-glucoside
  • Octanethioic acid S-propyl ester
  • Hexanethioic acid S-decyl ester
  • Thiopropionic acid S-undecyl ester
  • trisporic acid
  • 4-[(2-Carboxy-3-methylphenyl)methoxy]benzeneacetic acid
  • Benzonitrile,4-[[(2,3-dihydro-1-oxo-1h-isoindol-5-yl)oxy]methyl]-
  • 5-Methyl-7H-indeno[2,1-a]anthracene-7,12(13H)-dione
  • 4-bromo-N-(2-(furan-2-yl)-2-(thiophen-2-ylsulfonyl)ethyl)benzenesulfonamide
  • 8-(3-Chlorophenyl)-1,4-dioxa-8-azaspiro[4.5]decane
  • 2-(Iodomethyl)-5-(3-nitrophenyl)-1,3,4-oxadiazole
  • 7-Chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine
  • 2-[(3-Chlorophenyl)amino]acetaldehyde
  • 5,6-Dimethoxyindane-2-carboxylic acid
  • 2-(2-Iodoethyl)indane
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