Loroglossin

CAS# 58139-22-3

Loroglossin

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Chemical structure

Loroglossin

3D structure

Chemical Properties of Loroglossin

Cas No. 58139-22-3 SDF Download SDF
PubChem ID 185907 Appearance Powder
Formula C34H46O18 M.Wt 742.7
Type of Compound Other NPs Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R,3S)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate
SMILES CC(C)CC(C(C(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)O)(C(=O)OCC3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey QABASLXUKXNHMC-PIFIRMJRSA-N
Standard InChI InChI=1S/C34H46O18/c1-16(2)11-34(46,33(45)48-15-18-5-9-20(10-6-18)50-32-28(42)26(40)24(38)22(13-36)52-32)29(43)30(44)47-14-17-3-7-19(8-4-17)49-31-27(41)25(39)23(37)21(12-35)51-31/h3-10,16,21-29,31-32,35-43,46H,11-15H2,1-2H3/t21-,22-,23-,24-,25+,26+,27-,28-,29-,31-,32-,34-/m1/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.

Loroglossin Dilution Calculator

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Loroglossin Molarity Calculator

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Preparing Stock Solutions of Loroglossin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.3464 mL 6.7322 mL 13.4644 mL 26.9288 mL 33.661 mL
5 mM 0.2693 mL 1.3464 mL 2.6929 mL 5.3858 mL 6.7322 mL
10 mM 0.1346 mL 0.6732 mL 1.3464 mL 2.6929 mL 3.3661 mL
50 mM 0.0269 mL 0.1346 mL 0.2693 mL 0.5386 mL 0.6732 mL
100 mM 0.0135 mL 0.0673 mL 0.1346 mL 0.2693 mL 0.3366 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 Loroglossin

[Constituents of Gymnadenia conopsea].[Pubmed:21322946]

Zhongguo Zhong Yao Za Zhi. 2010 Nov;35(21):2852-61.

OBJECTIVE: To investigate the chemical constituents of tuber of Gymnadenia conopsea. METHOD: The constituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis. RESULT: Thirty-four compounds were isolated. Their structures were identified as six 2-isobutyltartrate benzyl ester glucosides: coelovirin A (1), coelovirin B (2), coelovirin E (3), coelovirin D (4), dactylorhin B (5) and Loroglossin (6). Three 2-isobutylmalate benzyl ester glucosides: dactylorhin A (7), dactylorhin E (8) and militarine (9). Three lignans: arctigenin (10), lappaol A (11) and lappaol F (12). Six aromatic acid (alhyde or alcohol) derivatives: 4-beta-D-glucopyranosyloxyl-trans-phenylpropenoic acid (13), 4-beta-D-glucopyranosyloxyl-cis-phenylpropenoic acid (14), gastrodin (15), 4-beta-D-glucopyranosyloxylphenylaldehyde (16), 4-beta-D-glucopyranosyloxylbenzyl methyl ether (17), 4-beta-D-glucopyranosyloxyloxylbenzyl ethyl ether (18), and bis(4-hydroxybenzyl) ether mono 4-O-beta-D-glucopyranoside (19). Four cyclodipeptides: cyclo(L-Leu-L-Tyr) (20), cyclo(L-Leu-L-Pro) (21), cyclo(L-Val-L-Tyr) (22), and cyclo(L-Ala-D-Phe) (23). One N6-substituted andenosine: N6-(4-hydroxybenzyl)-adenine riboside (24). An aromatic amide: N-trans-feruloyltyramine (25). Nine aromatic acids (or aldehyde or alcohol): 3-hydroxybenzoic acid (26), 4-hydroxyisophthalic acid (27), 4-hydroxybenzyl alcohol (28), 4-hydroxybenzyl methyl ether (29), 4-hydroxybenzylaldehyde (30), 4-hydroxybenzoic acic (31), 4-hydroxy-3-methoxybenzoic acid (32), trans-p-hydroxyphenylpropenoic acid (33), and cis-p-hydroxyphenylpropenoic acid (34). At a concentration of 1.0 x 10(-6) mol x L(-1), compounds 10-12 showed antioxidative activity inhibiting Fe(+2) -cystine induced rat liver microsomal lipid peroxidation with inhibitory rates of 53%, 59%, and 52%, respectively(positive control VE with 35% inhibition). CONCLUSION: These compounds were obtained from the genus Gymnadenia for the first time except for 5-7, 9, 15, 28-34. Compounds 10-12 possess antioxidant activity.

[Quantitative analysis of four active constituents in Tibetan herb Gymnadenia conopsea by high-performance liquid chromatography].[Pubmed:19894516]

Zhongguo Zhong Yao Za Zhi. 2009 Jul;34(14):1819-22.

OBJECTIVE: To develop a high performance liquid chromatography method for simultaneous determination of tour active constituents, dactylorhin B, Loroglossin, dactylorhin A, militarine present in a Tibetan herb Gymnadenia conopsea. METHOD: The analysiswas achieved on a Pravil C18 column (4.6 mm x 150 mm, 5 microm) eluted with the mobile phases of methanol (A)-water (B) in gradient elution. The initial condition was 15% A, chsnhrf to 20% A in 10 min, to 45% A in 10 min, to 70% A in 15 min. The detection wavelength was set at 222 nm. The flow rate was 0.7 mL x min(-1). Orthogonal test was adopted to optimize extraction process of four active compounds from Gymnadenia conopsea. RESULT: The assay displayed good linearity over the concentration ranges of 0.20-4.05 microg (r = 0.9999), 0.10-5.11 micro g (r = 0.9999), 0.10-5.11 microg (r = 0.9999) and 0.09-1.79 microg (r = 0.9999), respectively. The average recoveries (n=9) were 99.19%, 99.16%, 99.52% and 99.00% for dactylorhin B, Loroglossin, dactylorhin A and militarine respectively. CONCLUSION: The method is simple, sensitive, reliable and reproducible which can be used for the quality study of Gymnadenia conopsea.

Quantitative determination of five glucosyloxybenzyl 2-isobutylmalates in the tubers of Gymnadenia conopsea and Coeloglossum viride var. bracteatum by HPLC.[Pubmed:19772750]

J Chromatogr Sci. 2009 Sep;47(8):709-13.

Glucosyloxybenzyl 2-isobutylmalates are one group of important active constituents in the tubers of Gymnadenia conopsea R. Br. and Coeloglossum viride (L.) Hartm. var. bracteatum (Willd.). For the purpose of quality evaluation of these two Chinese herbal medicines, it is necessary to use a rapid and reliable assay that is suitable for the determination of their active constituents. A high-performance liquid chromatography method is firstly developed for the simultaneous quantification of five glucosyloxybenzyl 2-isobutylmalates in the tubers. The analytes including dactylorhin B, dactylorhin E, Loroglossin, dactylorhin A, and militarine are isolated from the tubers of G. conopsea. The compounds are separated on an Agilent Hydrosphere C(18) (150 x 4.6 mm i.d., 5 microm) column using a mobile phase of acetonitrile-water including 0.3% acetic acid (adjusted with 36% acetic acid) with gradient elution at a flow rate of 1.0 mL/min. Detection is set at a UV wavelength of 221.5 nm. The recovery of the method is 97.7-101.0%, and linearity (r > 0.9998) is obtained for all the analytes. The assay is successfully applied to determine the contents of the analytes in the tubers of G. conopsea and C. viride var. bracteatum collected from different regions of China.

[Chemical constituents from the tuber of Cremastra appendiculata].[Pubmed:18507346]

Yao Xue Xue Bao. 2008 Feb;43(2):181-4.

To study the chemical constituents of "Shan-Ci-Gu" (the tuber of Cremastra appendiculata (D. Don) Makino), the compounds were isolated with silica gel and reverse phase silica gel as well as Sephadex column chromatographic method. Their structures were elucidated on the basis of modern spectra technology. Seven compounds were isolated and identified as 5-methoxybibenzyl-3, 3'-di-O-beta-D-glucopyranoside (1), militarine (2), Loroglossin (3), protocatechuic acid (4), succinic acid (5), gastrodin (6), and daucosterol (7). Compound 1 is a new compound. Compounds 2 -6 were isolated from this plant for the first time.

Chemical fingerprint analysis of rhizomes of Gymnadenia conopsea by HPLC-DAD-MSn.[Pubmed:16934540]

J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Dec 5;844(2):301-7.

A high-performance liquid chromatography-diode array detection-tandem mass spectrometry (HPLC-DAD-MS(n)) method has been firstly developed for chemical fingerprint analysis of rhizomes of Gymnadenia conopsea R. Br. and rapid identification of major compounds in the fingerprints. Comparing the UV and MS spectra with those of reference compounds, seven main peaks in the fingerprints were identified as adenosine (1), 4-hydroxybenzyl alcohol (2), 4-hydroxybenzyl aldehyde (3), dactylorhin B (4), Loroglossin (5), dactylorhin A (6) and militarine (7). Compounds 4-7 were succinate derivative esters and firstly discovered from this species. The Computer Aided Similarity Evaluation System (CASES) for chromatographic fingerprint of traditional Chinese medicine was employed to evaluate the similarities of 10 samples of the rhizomes of G. conopsea collected from Sichuan, Qinghai and Hebei provinces, Tibet autonomous region of China, and Nepal. These samples from different sources had similar chemical fingerprints. This method is specific and may serve for quality identification and comprehensive evaluation of this traditional Tibetan remedy.

Chemical constituents of the rhizomes of Coeloglossum viride var. bracteatum.[Pubmed:14989381]

J Asian Nat Prod Res. 2004 Mar;6(1):49-61.

Seven new compounds, named coelovirins A-G (1-7), along with fourteen known constituents were isolated from the rhizomes of Coeloglossom viride var. bracteatum (Orchidaceae). On the basis of chemical and spectroscopic methods, including 2D-NMR techniques, the structures of new compounds were elucidated as 1-(4-beta-D-glucopyranosyloxybenzyl)-(2R,3S)-2-isobutyltartrate (1), 4-(4-beta-glucopyranosyloxybenzyl)-(2R,3S)-2-isobutyltartrate (2), 1-(4-beta-D-glucopyranosyloxybenzyl)-(2R,3S)-2-beta-D-glucopyranosyl-2-isobutylta rtrate (3), 4-(4-beta-D-glucopyranosyloxybenzyl)-(2R,3S)-2-beta-D-glucopyranosyl-2-isobutylta rtrate (4), (2R,3S)-2-beta-D-glucopyranosyl-2-isobutyltartaric acid (5), bis(4-beta-D-glucopyranosyloxybenzyl)-(2R,3S)-2-[beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranosyl]-2-isobutyltartrate (6) and bis(4-beta-D-glucopyranosyloxybenzyl)-(2R)-2-[beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranosyl]-2-isobutylmalate (7). The known compounds are 4-hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, 4,4'-dihydroxydibenzyl ether, 4,4'-dihydroxydiphenylmethane, 4-(4-hydroxybenzyloxy)benzyl alcohol, gastrodin, quercetin-3,7-diglucoside, thymidine, Loroglossin, militarine, dactylorhin A, dactylorhin B, beta-sitosterol and daucosterol.

[Studies on the chemical constituents of Coeloglossum viride (L.) Hartm. var. bracteatum (Willd.) Richter].[Pubmed:12579762]

Yao Xue Xue Bao. 2002 Mar;37(3):199-203.

AIM: To study the chemical constituents of the rhizomes of Coeloglossum viride (L.) Hartm. var. bracteatum (Willd.) Richter. METHODS: The compounds were mainly isolated with normal phase and reverse phase column chromatographic methods and HPLC. Their structures were elucidated on the basis of physical constants and spectral analysis (UV, IR, EI-MS, positive and negative FAB-MS, APCI-MS, 1HNMR, 13CNMR, DEPT, 1H-1H COSY, HMQC and HMBC). RESULTS: Eight compounds were obtained from the ethanolic extract of the rhizomes of this plant, dactylorhin B (I), Loroglossin (II), dactylorhin A (III), militarine (IV), coelovirin A (V), gastrodin (VI), thymidine (VII) and quercetin-3,7-di-O-beta-D-glucopyranoside (VIII). CONCLUSION: All the compounds were obtained from this plant and genus Coeloglossum for the first time. V named coelovirin A, is a new compound.

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