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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H16O8
Molecular Weight 360.3155
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ROSMARINIC ACID

SMILES

c1cc(c(cc1/C(/[H])=C(\[H])/C(=O)O[C@]([H])(Cc2ccc(c(c2)O)O)C(=O)O)O)O

InChI

InChIKey=DOUMFZQKYFQNTF-WUTVXBCWSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H16O8
Molecular Weight 360.3155
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 1
Optical Activity UNSPECIFIED

Rosmarinic acid (α-o-caffeoyl-3,4-dihydroxyphenyllactic acid; RA) is a naturally occurring hydroxylated compound commonly found in species of the subfamily Nepetoideae of the Lamiaceae and Boraginaceae, such as Rosmarinus officinalis, Salvia officinalis, and Perilla frutescens. RA is biosynthesized from the amino acids L-phenylalanine and L-tyrosine by eight enzymes that include phenylalanine ammonia lyase and cinnamic acid 4-hydroxylase. Recently, RA and its derivatives have attracted interest for their biological activities, which include anti-inflammatory, anti-oxidant, anti-angiogenic, anti-tumor, and anti-microbial functions. Clinically, RA attenuates T cell receptor-mediated signaling, attenuates allergic diseases like allergic rhinitis and asthma, and 2,4-dinitrofluorobenzene-induced atopic dermatitis-like symptoms, protects from neurotoxicity, and slows the development of Alzheimer's disease. Rosmarinic Acid seems to be able to suppress 5-lipoxygenase and 5-HETE synthesis (a pro-inflammatory compound in the omega-6 metabolic chain). Rosmarinic acid appeared to be effective in suppressing allergies in a dose-dependent manner, with 30% of the placebo group reporting symptom relief compared to 55.6% of the 50mg group and 70% of the 200mg group.

CNS Activity

Curator's Comment:: Rosmarinic acid ameliorates depressive-like behaviors in a rat model of CUS and Up-regulates BDNF levels in the hippocampus and hippocampal-derived astrocytes.

Originator

Curator's Comment:: Rosmarinic acid is a naturally occurring polyphenolic compound that was first discovered in 1958 by the Italian scientists M. L. Scarpatti and and G. Oriente

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
50.1 µM [IC50]
184.6 µM [IC50]
26.7 µM [IC50]
1.3 µM [IC50]
550.0 nM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action.
1997 Sep 12
HIV-1 integrase inhibitory substances from Coleus parvifolius.
2003 Mar
Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet.
2005
Rosmarinic acid as a downstream inhibitor of IKK-beta in TNF-alpha-induced upregulation of CCL11 and CCR3.
2006 Jun
The effect of dietary polyphenols on the epigenetic regulation of gene expression in MCF7 breast cancer cells.
2010 Feb 1
Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus.
2013
Patents

Sample Use Guides

A human study consisting of 30 persons aged 21-53 with mild cedar allergies (who get stuffy noses during allergy season) were given either 50mg Rosmarinic acid, 200mg, or placebo to be taken with breakfast for 21 days. Rosmarinic acid appeared to be effective in suppressing allergies in a dose-dependent manner, with 30% of the placebo group reporting symptom relief compared to 55.6% of the 50mg group and 70% of the 200mg group.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: Rosmarinic acid shows antioxidant effects against hydroxyl (HO(•)) and nitric oxide (NO) radicals (IC50 of 29.4 and 140 uM, respectively), and inhibition of lipid peroxidation (IC50 of 19.6 uM). https://www.ncbi.nlm.nih.gov/pubmed/27270453
Rosmarinic acid (RA) exerts a significant cytoprotective effect by scavenging intracellular ROS induced by UVB. In H2O2-treated cells, 2.5 uM Rosmarinic acid scavenges 60% of intracellular ROS compared to 77% of intracellular ROS scavenging effect in N-acetyl-L-cysteine (NAC)
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:06:07 UTC 2021
Edited
by admin
on Sat Jun 26 14:06:07 UTC 2021
Record UNII
MQE6XG29YI
Record Status Validated (UNII)
Record Version
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Name Type Language
ROSMARINIC ACID
HSDB   INCI   MI   USP-RS  
INCI  
Official Name English
BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-
Common Name English
MEIJI RED PERILLA POLYPHENOL
Brand Name English
RM-21A
Code English
NPLC-0542
Code English
ORISTRACT ROA
Brand Name English
LABIATENIC ACID
Common Name English
ROSMARINIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Common Name English
ROSMARINIC ACID [HSDB]
Common Name English
BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-
Common Name English
LABIATIC ACID
Common Name English
ROSMARINIC ACID [USP-RS]
Common Name English
ROSMARINIC ACID [INCI]
Common Name English
ROSMARINIC ACID (CONSTITUENT OF ROSEMARY) [DSC]
Common Name English
ROSMARINIC ACID [MI]
Common Name English
TRANS-ROSMARINIC ACID
Common Name English
ROSEMARY ACID
Common Name English
CINNAMIC ACID, 3,4-DIHYDROXY-, 2-ESTER WITH 3-(3,4-DIHYDROXYPHENYL)LACTIC ACID
Common Name English
Classification Tree Code System Code
DSLD 1943 (Number of products:10)
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
Code System Code Type Description
CAS
20283-92-5
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY
WIKIPEDIA
ROSMARINIC ACID
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY
HSDB
537-15-5
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY
CAS
537-15-5
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
FDA UNII
MQE6XG29YI
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY
USP_CATALOG
1605952
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY USP-RS
MESH
C041376
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY
EVMPD
SUB125758
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY
PUBCHEM
5281792
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY
MERCK INDEX
M9669
Created by admin on Sat Jun 26 14:06:07 UTC 2021 , Edited by admin on Sat Jun 26 14:06:07 UTC 2021
PRIMARY Merck Index
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