Rosmarinic acid Chemical Properties

Melting point:

171-175 °C (lit.)

alpha 

+102～+110°(D/20℃)(c=0.2,C2H5OH)

Boiling point:

694.7±55.0 °C(Predicted)

Density 

1.33

storage temp. 

2-8°C

solubility 

Soluble in ethanol, DMSO or dimethyl formamide to approximately 25 mg/mL.

form 

powder

pka

2.78±0.10(Predicted)

color 

white to faintly beige

BRN 

2227587

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.

InChI

InChI=1/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-/s3

InChIKey

DOUMFZQKYFQNTF-WUTVXBCWSA-N

SMILES

C(C1C=CC(O)=C(O)C=1)[C@H](C(=O)O)OC(=O)/C=C/C1C=CC(O)=C(O)C=1 |&1:9,r|

LogP

0.871 (est)

CAS DataBase Reference

20283-92-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

WGK Germany 

3

RTECS 

GD8990000

F 

10-23

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich

Rosmarinic acid Usage And Synthesis

Uses

1. Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. However, it is also found in species of other higher plant families and in some fern and hornwort species. Rosmarinic acid has a number of interesting biological activities, e.g. antiviral, antibacterial, antiinflammatory and antioxidant. The presence of rosmarinic acid in medicinal plants, herbs and spices has beneficial and health promoting effects. In plants, rosmarinic acid is supposed to act as a preformed constitutively accumulated defence compound.[sciencedirect]
2. Rosmarinic acid (RA) is one example of a naturally occurring phenolic compound in plants. RA is especially high in Salvia officinalis (garden sage). As an antioxidant, RA possesses both health benefits, and is useful as a food additive to keep foods fresh.Recently, Bakota et al. successfully prepared an extract of Salvia officinalis at three times the levels from sage leaves alone.[thermofisher]
3. Rosmarinic Acid is a phenylpropanoid isolated from Labiatae herbs. The compound exhibits antiinflammatory activity and inhibits the proliferation of murine mesangial cells. Rosmarinic Acid has been shown to dose dependently inhibit migration, adhesion, and invasion of Ls174-T human colon carcinoma cells. Rosmarinic Acid has been documented to increase the melanin content in B16 melanoma cells through activation of protein kinase A. In the same study rosmarinic acid induced the phosphorylation of CRE-binding protein (CREB) and activated cAMP response element (CRE). In the classical complement pathway Rosmarinic Acid inhibited C3-convertase. It also has shown to be an activator of GPR35.[Santa Cruz]
4. Rosmarinic acid is a naturally-occurring phenolic compound with antioxidant and anti-inflammatory properties. This compound inhibits lipid peroxidation of rat liver microsomes by 90% at a concentration of 25 µg/ml.Rosmarinic acid suppresses endotoxin-induced activation of complement and concomitant formation of prostacyclin.Formation of 5-HETE and LTB from human PMNL is inhibited by rosmarinic acid at concentrations of 10-5 to 10-3 M. [caymanchem]

Rosmarinus officinalis

Rosmarinus officinalis belongs to genus Rosmarinus and family Lamiaceae. This plant is a small evergreen shrub, about 1 meter high, and young shoots are 4-sided and closely arranged, with dense hairs; leaves opposite, sessile, leathery, linear, with surface dark green and smooth, and leaf back gray and finely hairy; Flowers bisexual, paired grown on short stalk, axillary, calyx bell-shaped, two lips, with upper lip entire and lower lip two-lobed; corolla 3 times longer than calyx, 2 lips, with upper lip furrow into two-lobs and lower lip concavely tri-lobed to the middle; 2 fertile stamens that extend out of the flower; flowers pale blue color, sometimes pink or white; flowers in spring, with a rich aroma.
Rosmarinus officinalis is native to the North Africa and was transported to China after Zhang Qian went to the Western Regions, and it was a traditional commodity among Roman Empire, the Eastern Roman Empire and China, that’s why Chinese also called it "the Daqin aroma."
This plant is both a medicinal and edible herb with an oil body, and it is available for viewing and extracting aroma, and the fresh twigs and buds of rosemary can be used also to extract aromatic oils. This aromatic oil is used in deployment of food flavor and seasoners and the production of sauce. As a food seasoner, Rosmarinus officinalis is seldom used in Chinese food but mainly in western food, it is quite common in Europe, and is still a very popular cooking spice in Europe so far.

Figure 1 The Photo of Rosmarinus officinalis
Rosmarinus officinalis is a historic spice plant, which is native to the Mediterranean coast. It was first introduced to China in 1981 by the Chinese Academy of Sciences and with the successful cultivation, and now has been grown in Yunnan, Hunan, Sichuan, Guizhou, Guangxi and other places. Rosmarinus officinalis is a valuable natural aromatic plant, and in the growing season it will emit a kind of fragrance smell with the function of purifying heart and refreshing spirits. Its stems, leaves and flowers have a pleasant scent, and aromatic oil that extracted from flowers and twigs can be used to deploy air cleaners, perfumes, soaps and other cosmetics. The most famous lotion is made with rosemary, and it can be used in beverages, skin care oils, hair tonic, washing paste. As a medicine, it can be used in treatment of neurological disorders and in ointment production to treat headache and rheumatism. In recent years, it has also been found to be an ideal natural preservative. It also can be planted or potted as ornamental plants.
Rosmarinus officinalis is a versatile commercial crop, from which antioxidants and rosemary essential oils and pharmaceutical intermediates can be extracted.
Antioxidants are powdery substance that extracted from Rosmarinus officinalis; with the main ingredients with antioxidant function are phenolic, acids, and flavonoids and so on.
rosemary essence oil is a kind of liquid oil consisting of 30 kinds of volatile components.
The powdery extract substance rosmarinic acid from Rosmarinus officinalis has an efficient, non-toxic antioxidant effect and can be widely used in food, functional foods, spices and condiments and household chemicals industries.

Antimicrobial activity

Rosmarinic acid has a broad-spectrum anti-microbial activity against bacteria and fungi. Rosmarinic acid can significantly inhibit Bacillus subtilis, Micrococcus luteus, Escherichia coli, Staphylococcus aureus and Rhizoctonia and other bacteria. Neusa found that rosmarinic acid could inhibit the growth of Streptococcus mutans and Caries streptococci and the formation of biological membrane, reducing their glucose transferase activity, which indicating that rosmarinic acid can be used for oral disease prevention and treatment. Studies in mechanism of antibacterial activity of rosmarinic acid showed: on the one hand, rosmarinic acid can increase the permeability of the bacterial cell membrane, resulting in a lot of leakage of carbohydrates and protein, affecting the normal metabolism of bacteria; on the other hand, it can also affect protein metabolism of bacteria, and also inhibit Taq DNA polymerase.
Guo Daosen studied the inhibition effects of rosmarinic acid on mycelial growth and spore germination of different plant pathogenic fungi, and found that rosmarinic acid had stronger inhibition on mycelial growth of tomato Botrytis cinerea, mango gray leaf spot pathogen, citrus Penicillium and pear Alternaria panax, with the strongest inhibition in spore germination of pear Alternaria panax.
Rosmarinic acid has antibacterial activity on both the Gram-negative bacteria E. coli and the Gram-positive bacteria Staphylococcus aureus, but the sensitivity of S. aureus to rosmarinic acid is significantly higher than that of E. coli. The results also show that rosmarinic acid can significantly increase the permeability of the bacterial cell membrane, accelerate the leakage of carbohydrate and protein, and cause disorder of the cell metabolism. Rosmarinic acid can affect protein metabolism of bacteria. By comparing the total protein in Staphylococcus aureus before and after the treatment of rosmarinic acid, it is known that treatment of rosmarinic acid promotes degradation of certain proteins in bacterial metabolism, or promotes the synthesis of certain proteins in short term. As for which specific protein is affected by rosmarinic acid, further identification is still needed. Through the experimental results of interaction between rosmarinic acid and plasmid DNA, we know that rosmarinic acid does not interact with DNA, whereby it can be speculated that rosmarinic acid can not bind with the primers in the polymerase chain reaction system, thus rosmarinic acid inhibits polymerization chain reaction because this compound inhibits the binding activity of the DNA polymerase, thereby inhibiting the replication of DNA. In summary, rosmarinic acid has a certain influence on the permeability of cell membrane, protein metabolism and DNA replication in bacteria, and thus plays its anti-bacteria effect.
The above information is edited by the Chemicalbook of Cheng Jingmin.

Description

Rosmarinic acid (20283-92-5) displays radical scavenging1, anti-inflammatory2 and amyloid-β aggregation inhibition activities.3 Rosmarinic acid has also been shown to act as an agonist at GPR35.4

Chemical Properties

White to off-white powder

Uses

Rosmarinic Acid is a phenolic compound with antioxidant and anti-inflammatory activity. Rosmarinic Acid has been shown to inhibit againts peroxidative damage to biomembranes. Rosmarinic Acid also supp resses endotoxin-induced activation of complement and concomitant prostacyclin biosynthesis.

Uses

An activator of GPR35.

Uses

Rosmarinic acid is a naturally-occurring phenolic compound with antioxidant and anti-inflammatory properties. This compound inhibits lipid peroxidation of rat liver microsomes by 90% at a concentration of 25 μg/ml. Rosmarinic acid suppresses endotoxin-induced activation of complement and concomitant formation of prostacyclin. Formation of 5-HETE and LTB4 from human PMNL is inhibited by rosmarinic acid at concentrations of 10-5 to 10-3 M.

Definition

ChEBI: (R)-rosmarinic acid is a stereoisomer of rosmarinic acid having (R)-configuration. It has a role as a plant metabolite and a geroprotector. It is a conjugate acid of a (R)-rosmarinate. It is an enantiomer of a (S)-rosmarinic acid.

General Description

Rosmarinic acid is a bioactive plant phenolic compound with antioxidant and anti-inflammatory effects.

Biological Activity

Anti-inflammatory, cytostatic and antiviral.

Biochem/physiol Actions

Rosmarinic acid has shown to contain antioxidant, anti-inflammatory and antimicrobial activities. Possesses promising physiological actions related to cognitive performance, Alzheimer′s disease prevention, kideney disease treatment, cardioprotection and cancer chemoprevention.

Mode of action

Rosmarinic acid (RA), a water-soluble polyphenolic compound with antioxidant and anti-inflammatory properties. Inhibits several complement-dependent inflammatory processes via inhibition of the C5 convertase. Anticarcinogenic. Inhibitor of lipid peroxidation, TCR-induced T cell activation and proliferation.?

References

1) Miliauskas et al. (2005), Identification of radical scavenging compounds in Rhaponticum carthamoides by means of LC-DAD-SPE-NMR; J. Nat. Prod., 68 168 2) Sahu et al. (1999), Inhibition of complement by covalent attachment of rosmarinic acid to activated C3b; Biochem. Pharmacol, 57 1439 3) Ono et al. (2012), Phenolic compounds prevented amyloid β-protein oligomerization and synaptic dysfunction by site-specific binding; J. Biol. Chem., 287 14631 4) Deng et al. (2012), Multiple tyrosine metabolites are GPR35 agonists; Sci. Rep., 2 373

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