Rosmanol

CAS# 80225-53-2

Rosmanol

Catalog No. BCN8425----Order now to get a substantial discount!

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Quality Control of Rosmanol

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Chemical structure

Rosmanol

3D structure

Chemical Properties of Rosmanol

Cas No. 80225-53-2 SDF Download SDF
PubChem ID 13966122 Appearance White-beige powder
Formula C20H26O5 M.Wt 346.42
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility DMSO : 150 mg/mL (433.00 mM; Need ultrasonic)
SMILES CC(C)C1=C(C(=C2C(=C1)C(C3C4C2(CCCC4(C)C)C(=O)O3)O)O)O
Standard InChIKey LCAZOMIGFDQMNC-FORWCCJISA-N
Standard InChI InChI=1S/C20H26O5/c1-9(2)10-8-11-12(15(23)13(10)21)20-7-5-6-19(3,4)17(20)16(14(11)22)25-18(20)24/h8-9,14,16-17,21-23H,5-7H2,1-4H3/t14-,16+,17-,20-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Rosmanol

1 Salvia sp.

Biological Activity of Rosmanol

Description1. Rosmanol has antioxidant activity, it can activate the antioxidant response element. 2. Rosmanol has biphasic modulation of GABAA receptors, demonstrates CNS activity in mouse models of antinociception, antidepressant and anxiolysis. 3. Rosmanol exhibits significant cytotoxicity towards the neuroblastoma cells. 4. Rosmanol potently induces apoptosis through both the mitochondrial apoptotic pathway and death receptor pathway in human colon adenocarcinoma COLO 205 cells. 5. Rosmanol has anti-inflammatory activity, it potently inhibits lipopolysaccharide-induced iNOS and COX-2 expression through downregulating MAPK, NF-kappaB, STAT3 and C/EBP signaling pathways.
TargetsGABA Receptor | Nrf2 | PARP | Bcl-2/Bax | Caspase | NOS | COX | PGE | STAT | ERK | p38MAPK | PI3K | Akt | NF-kB

Rosmanol Dilution Calculator

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Rosmanol Molarity Calculator

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Preparing Stock Solutions of Rosmanol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8867 mL 14.4333 mL 28.8667 mL 57.7334 mL 72.1667 mL
5 mM 0.5773 mL 2.8867 mL 5.7733 mL 11.5467 mL 14.4333 mL
10 mM 0.2887 mL 1.4433 mL 2.8867 mL 5.7733 mL 7.2167 mL
50 mM 0.0577 mL 0.2887 mL 0.5773 mL 1.1547 mL 1.4433 mL
100 mM 0.0289 mL 0.1443 mL 0.2887 mL 0.5773 mL 0.7217 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Rosmanol

NMR, HS-SPME-GC/MS, and HPLC/MS(n) Analyses of Phytoconstituents and Aroma Profile of Rosmarinus eriocalyx.[Pubmed:28657166]

Chem Biodivers. 2017 Oct;14(10).

In this work, a comprehensive study on the chemical constituents of the aerial parts of Rosmarinus eriocalyx (Lamiaceae), an aromatic shrub traditionally consumed as a food and herbal remedy in Algeria, is presented. The aroma profile was analysed by headspace solid phase microextraction (HS-SPME) coupled with gas chromatography-mass spectrometry (GC/MS), whereas the crude extract constituents were analyzed by (1) H-NMR and by high performance liquid chromatography coupled with mass spectrometry (HPLC/MS(n) ). Thirty-nine volatile compounds, most of them being monoterpenes, have been identified, with camphor, camphene, and alpha-pinene as the most abundant constituents. (1) H-NMR analysis revealed the presence of phenolic compounds and betulinic acid while HPLC/MS(n) allowed the identification of glycosilated and aglyconic flavonoids as well as phenylpropanoid derivatives. Some of these constituents, namely as betulinic acid, Rosmanol, and cirsimaritin were reported for the first time in R. eriocalyx.

Diterpenes from rosemary (Rosmarinus officinalis): Defining their potential for anti-cancer activity.[Pubmed:26170168]

Cancer Lett. 2015 Oct 28;367(2):93-102.

Recently, rosemary extracts standardized to diterpenes (e.g. carnosic acid and carnosol) have been approved by the European Union (EU) and given a GRAS (Generally Recognized as Safe) status in the United States by the Food and Drug Administration (FDA). Incorporation of rosemary into our food system and through dietary selection (e.g. Mediterranean Diet) has increased the likelihood of exposure to diterpenes in rosemary. In consideration of this, a more thorough understanding of rosemary diterpenes is needed to understand its potential for a positive impact on human health. Three agents in particular have received the most attention that includes carnosic acid, carnosol, and Rosmanol with promising results of anti-cancer activity. These studies have provided evidence of diterpenes to modulate deregulated signaling pathways in different solid and blood cancers. Rosemary extracts and the phytochemicals therein appear to be well tolerated in different animal models as evidenced by the extensive studies performed for approval by the EU and the FDA as an antioxidant food preservative. This mini-review reports on the pre-clinical studies performed with carnosic acid, carnosol, and Rosmanol describing their mechanism of action in different cancers.

New terpenoid glycosides obtained from Rosmarinus officinalis L. aerial parts.[Pubmed:25200369]

Fitoterapia. 2014 Dec;99:78-85.

Five new terpenoid glycosides, named as officinoterpenosides A(1) (1), A(2) (2), B (3), C (4), and D (5), together with 11 known ones, (1S,4S,5S)-5-exo-hydrocamphor 5-O-beta-D-glucopyranoside (6), isoRosmanol (7), Rosmanol (8), 7-methoxyRosmanol (9), epiRosmanol (10), ursolic acid (11), micromeric acid (12), oleanolic acid (13), niga-ichigoside F(1) (14), glucosyl tormentate (15), and asteryunnanoside B (16), were obtained from the aerial parts of Rosmarinus officinalis L. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D and 2D NMR). Among the new ones, 1 and 2, 3 and 4 are diterpenoid and triterpenoid glycosides, respectively; and 5 is a normonoterpenoid. For the known ones, 6 was isolated from the Rosmarinus genus first, and 15, 16 were obtained from this species for the first time.

Determination and Pharmacokinetic Study of Three Diterpenes in Rat Plasma by UHPLC-ESI-MS/MS after Oral Administration of Rosmarinus officinalis L. Extract.[Pubmed:28587218]

Molecules. 2017 Jun 4;22(6). pii: molecules22060934.

Rosmarinus officinalis L. is commonly used as a spice and flavoring agent. Diterpenes are the main active compounds of R. officinalis. An Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry (UHPLC-ESI-MS/MS) method was developed for the determination of carnosol, Rosmanol, and carnosic acid isolated from R. officinalis in rat plasma, and applied to a pharmacokinetic study after oral administration of R. officinalis extract. Sample preparation involved a liquid-liquid extraction of the analytes with ethyl acetate. Butylparaben was employed as an internal standard (I.S.). Chromatographic separation was carried out on a C18 column (ACQUITY UPLC((R)) HSS T3, 1.8 mum, 2.1 mm x 100 mm) with a gradient system consisting of the mobile phase solution A (0.1% formic acid in water) and solution B (acetonitrile) at the flow rate of 0.3 mL/min. The quantification was obtained using multiple reaction monitoring (MRM) mode with electrospray ionization (ESI). The UHPLC-MS/MS assay was validated for linearity, accuracy, precision, extraction recovery, matrix effect and stability. This study described a simple, sensitive and validated UHPLC-MS/MS method for the simultaneous determination of three diterpene compounds in rat plasma after oral administration of R. officinalis extract, and investigated on their pharmacokinetic studies as well.

Relevance of the carnosic acid/carnosol ratio for the level of rosemary diterpene transfer and for improving lamb meat antioxidant status.[Pubmed:24423523]

Food Chem. 2014 May 15;151:212-8.

The aim of the present work was to evaluate whether the relation between the concentrations of the two major diterpenes present in two typified rosemary extracts affects their levels of deposition and antioxidant capacity in different lamb tissues. The composition of the extracts expressed as percentage of weight/weight was 1:1 (14-16)% and 2:1 (25-11)% (carnosic acid-carnosol), respectively. Thirty weaned lambs were assigned randomly to three homogeneous groups. One group was fed a basal diet as a control and the diets of the other two were enriched with rosemary extracts 1:1 and 2:1, respectively. HPLC-ESI-MS/TOF identified a metabolite (C19H22O3) described for the first time in lamb tissues, along with carnosol, carnosic acid, Rosmanol and carnosol-p-quinone. The results obtained corroborate the importance of the presence of carnosol in the dietary administration of rosemary extract as a way of improving the stability of the diterpene fraction during feed manufacturing and the level of deposition and antioxidant efficacy of diterpenes after ruminal fermentation.

[Identification of the chemical compositionsof Verbena officinalis L. extract by high performance liquid chromatography-photodiode array-high resolution mass spectrometry].[Pubmed:29048857]

Se Pu. 2017 Sep 8;35(9):987-994.

To investigate the main chemical compositions of Verbena officinals L. extract, a qualitative high performance liquid chromatography-photodiode array-high resolution mass spectrometry (HPLC-PDA-HRMS) method was established. The structures of the compounds detected were identified by analyzing the chromatographic profiles and the corresponding mass spectra obtained by full scan and MS(n) full scan. Twenty one compounds including iridoid glycosides, flavonoids, triterpenoids, phenylpropanoids and phenolic diterpenoids were identified, and six of them were not reported in other literatures about Verbena officinalis L. extract, such as carnosic acid, carnosol, Rosmanol, isoRosmanol, rosmarinic acid and acacetin-7-O-rutinoside. This method is simple, rapid, accurate and sensitive. It provides a reliable scientific basis for the identification of the authenticity and quality control of Chinese medicinal materials.

Phytochemical Profiling of Flavonoids, Phenolic Acids, Terpenoids, and Volatile Fraction of a Rosemary (Rosmarinus officinalis L.) Extract.[Pubmed:27869784]

Molecules. 2016 Nov 19;21(11). pii: molecules21111576.

This paper presents a comprehensive analysis of the phytochemical profile of a proprietary rosemary (Rosmarinus officinalis L.) extract rich in carnosic acid. A characterization of the (poly)phenolic and volatile fractions of the extract was carried out using mass spectrometric techniques. The (poly)phenolic composition was assessed by ultra-high performance liquid chromatography-electrospray ionization-mass spectrometry (UHPLC-ESI-MS(n)) and a total of 57 compounds were tentatively identified and quantified, 14 of these being detected in rosemary extract for the first time. The rosemary extract contained 24 flavonoids (mainly flavones, although flavonols and flavanones were also detected), 5 phenolic acids, 24 diterpenoids (carnosic acid, carnosol, and Rosmanol derivatives), 1 triterpenoid (betulinic acid), and 3 lignans (medioresinol derivatives). Carnosic acid was the predominant phenolic compound. The volatile profile of the rosemary extract was evaluated by head space solid-phase microextraction (HS-SPME) linked to gas chromatography-mass spectrometry (GC-MS). Sixty-three volatile molecules (mainly terpenes, alcohols, esters, aldehydes, and ketones) were identified. This characterization extends the current knowledge on the phytochemistry of Rosmarinus officinalis and is, to our knowledge, the broadest profiling of its secondary metabolites to date. It can assist in the authentication of rosemary extracts or rosemary-containing products or in testing its bioactivity. Moreover, this methodological approach could be applied to the study of other plant-based food ingredients.

Description

Rosmanol could inhibit the oxidation of low density lipoprotein (LPL) and significantly inhibit lipopolysaccharide induced iNOS and COX-2 expression, with anti-inflammatory effect.

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