ROSMARINIC ACID

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H16O8
Molecular Weight	360.3148
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C2=CC(O)=C(O)C=C2

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	360.3148
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25620368 | https://www.ncbi.nlm.nih.gov/pubmed/26114303 | https://examine.com/supplements/rosmarinic-acid/ | https://www.rosmarinic-acid.com/

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27270453	Inhibitor 8504	50.1 µM [IC50]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27270453	Inhibitor 8504	184.6 µM [IC50]
Catechol O-methyltransferase 21 Target ID: CHEMBL2023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27270453	Inhibitor 8504	26.7 µM [IC50]
Tyrosine-protein kinase FYN 7 Target ID: CHEMBL1841 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17315853	Inhibitor 8504	1.3 µM [IC50]
Integrase 2 Target ID: CHEMBL2366505 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12672152	Inhibitor 8504	550.0 nM [IC50]
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20149856	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Seasonal allergic rhinitis 64 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988517	Primary	Phase I 438	Unknown Approved Use Unknown
Nasal polyps 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00465543	Primary	Phase II 1147	Unknown Approved Use Unknown
Osteoarthritis of knee 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25058311 https://clinicaltrials.gov/ct2/show/NCT01380015	Primary	Phase IV 63	Unknown Approved Use Unknown
Atopic dermatitis 64 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19239556	Primary	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
72.22 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25978046/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	ROSMARINIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
162.2 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25978046/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	ROSMARINIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
142.2 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25978046/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	ROSMARINIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
354.88 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25978046/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	ROSMARINIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
832.13 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25978046/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	ROSMARINIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
945.03 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25978046/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	ROSMARINIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
500 mg 1 times / day multiple, oral Studied dose Dose: 500 mg, 1 times / day Route: oral Route: multiple Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33122694/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33122694/	Sources: https://pubmed.ncbi.nlm.nih.gov/33122694/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 UGT2B7 197 OAT1 725 UGT1A6 136 UGT1A1 246 CYP2E1 1060 CYP2C19 2057 P-gp 1741 BCRP 910 OAT3 747 OCT1 620 OCT2 779	CYP2E1 729 CYP1A2 1197 OAT1 395 OATP1B3 435 OCT1 393 CYP2C19 1119 UGT1A1 479 UGT1A6 343 UGT2B7 456 OAT3 391 OATP1B1 503 OCT2 434	BCRP 101 P-gp 301 MRP2 146

Drug as perpetrator

Target	Modality	Activity
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	moderate [IC50 19.1 uM]
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	moderate [IC50 23.4 uM]
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	moderate [IC50 9.24 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	no [IC50 >500 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	no [IC50 >500 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	unlikely [IC50 426 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	weak [IC50 39.6 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	weak [IC50 61 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	yes [IC50 1.52 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	yes [IC50 60.5 uM]
BCRP 985	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27422165/	yes
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32033628/	yes
MRP2 625	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27422165/	yes
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27422165/	yes
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32033628/	yes

Drug as victim

Target	Modality	Activity
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	no
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	no
OATP1B3 435	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	no
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	no
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	no
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33435470/	yes [Km 26.5 uM]
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	yes
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	yes
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	yes
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	yes
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30466000/	yes

PubMed

Title	Date	PubMed
Rosmarinic acid attenuates hepatic ischemia and reperfusion injury in rats.	2014-12	25455894
Inhibitors of the glyoxylate cycle enzyme ICL1 in Candida albicans for potential use as antifungal agents.	2014	24781056
Rosmarinic acid down-regulates endothelial protein C receptor shedding in vitro and in vivo.	2013-09	23774263
Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus.	2013	24358168
Protective effect of rosmarinic acid is through regulation of inflammatory cytokine in cadmium-induced ototoxicity.	2013	23548128
Frequent gene hypermethylation in laryngeal cancer cell lines and the resistance to demethylation induction by plant polyphenols.	2011-02	21078381
The effect of dietary polyphenols on the epigenetic regulation of gene expression in MCF7 breast cancer cells.	2010-02-01	19840838
Oxidative DNA damage protection and repair by polyphenolic compounds in PC12 cells.	2008-12-28	18996367
Rosmarinic acid as a downstream inhibitor of IKK-beta in TNF-alpha-induced upregulation of CCL11 and CCR3.	2006-06	16604092
Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry.	2005-06-05	15866491
Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet.	2005	16029149
Rosmarinic acid inhibits lung injury induced by diesel exhaust particles.	2003-04-15	12684091
HIV-1 integrase inhibitory substances from Coleus parvifolius.	2003-03	12672152
HIV integrase inhibitory activity of Agastache rugosa.	1999-10	10549582
Inhibition of complement by covalent attachment of rosmarinic acid to activated C3b.	1999-06-15	10353266
A search for anti-viral properties in Panamanian medicinal plants. The effects on HIV and its essential enzymes.	1999-01	10075118
Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action.	1997-09-12	9301668

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 19:07:43 GMT 2025` Edited by `admin` on `Mon Mar 31 19:07:43 GMT 2025`
Record UNII	MQE6XG29YI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEIJI RED PERILLA POLYPHENOL

Preferred Name

English

ROSMARINIC ACID

Official Name

English

BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-

Common 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 (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)