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β-D-mannopyranuronic acid, also known as D-mannuronic acid, is a monosaccharide derivative found in the polysaccharide alginate, which is extracted from brown seaweed. It is a uronic acid, meaning it is an oxidized form of a sugar, specifically the oxidation product of D-mannose. β-D-mannopyranuronic acid plays a crucial role in the structure and properties of alginate, which is used in various applications such as food thickeners, pharmaceuticals, and biotechnology. The molecule is characterized by its six-carbon sugar backbone in a pyranose ring structure, with a carboxylic acid group at the C-1 position.

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  • 33599-45-0 Structure
  • Basic information

    1. Product Name: β-D-mannopyranuronic acid
    2. Synonyms: β-D-mannopyranuronic acid
    3. CAS NO:33599-45-0
    4. Molecular Formula:
    5. Molecular Weight: 194.141
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 33599-45-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: β-D-mannopyranuronic acid(CAS DataBase Reference)
    10. NIST Chemistry Reference: β-D-mannopyranuronic acid(33599-45-0)
    11. EPA Substance Registry System: β-D-mannopyranuronic acid(33599-45-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 33599-45-0(Hazardous Substances Data)

33599-45-0 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 33599-45-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,5,9 and 9 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 33599-45:
(7*3)+(6*3)+(5*5)+(4*9)+(3*9)+(2*4)+(1*5)=140
140 % 10 = 0
So 33599-45-0 is a valid CAS Registry Number.

33599-45-0Relevant articles and documents

Hydrolysis behaviors of sugarcane bagasse pith in subcritical carbon dioxide-water

Liang, Jiezhen,Chen, Xiaopeng,Wang, Linlin,Wei, Xiaojie,Qiu, Feifei,Lu, Chaochao

, p. 99322 - 99330 (2016)

The aim of this study was to describe the hydrolysis behavior of sugarcane bagasse pith (SCBP) in subcritical CO2-water. The hydrolysis was carried out in a batch reactor using different temperatures (160 to 260 °C), liquid to solid ratios (20:1 to 100:1), CO2 pressures (0 to 7.3 MPa), stirring speeds (0 to 500 rpm) and reaction times (0 to 40 min). The highest total reducing sugar yield (43.6%) was obtained at 200 °C, liquid to solid ratio 30:1, 2 MPa CO2, 500 rpm and 50 min. Two-dimensional heteronuclear single quantum coherence (2D HSQC) nuclear magnetic resonance (NMR), scanning electron microscopy (SEM) and Fourier transform infrared spectrometry (FT-IR) were used to help elucidate the physical and chemical characteristics of the raw material and residual solid particles, with results consistent with the removal of hemicellulose during hydrolysis. The changes in the concentration of products with time were analyzed to understand product distribution through high-performance liquid chromatography (HPLC) and to infer the reaction mechanism.

Application of bacterial directed enzyme prodrug therapy as a targeted chemotherapy approach in a mouse model of breast cancer

Bahrami, Ahmad Reza,Hosseini-Giv, Niloufar,Matin, Maryam M.

, (2021/08/03)

Cancer is the second leading cause of death in the world. Some of the usual cancer treatments include surgery, chemotherapy, and radiotherapy. However, due to low efficacy and side effects of these treatments, novel targeted therapeutic methods are needed. One of the common drawbacks of cancer chemotherapy is off-target toxicity. In order to overcome this problem, many investigations have been conducted. One of the new targeted therapy methods known as bacterial directed enzyme-prodrug therapy (BDEPT) employs bacteria as enzyme carriers to convert a pro-drug to a drug specifically within the tumor site. In the present study, we used Escherichia coli DH5α carrying luxCDABE gene cluster and overexpressing β-glucuronidase for luminescent emission and enzyme expression, respectively. Enzyme expression can lead to the conversion of glycyrrhizic acid as a prodrug to glycyrrhetinic acid, a potent anti-cancer agent. DH5α-lux/βG was characterized and its stability was also evaluated. Bacteria colonization in the tumor site was measured by tissue homogenate preparation and colony counting method. Histopathological studies on the liver, spleen, and tumor were also conducted. According to the results, co-treatment of 4T1, a highly metastatic mouse breast cancer cell line, with GL and DH5α-lux/βG could significantly decrease the IC50 values. Moreover, increased number of bacteria could lead to a dramatic drop in IC50 value. Specific colonization of DH5α-lux/βG was observed in the tumor site compared with other tissues (p 0.0001). Moreover, the biocompatibility evaluation proved that DH5α-lux/βG had no adverse effects on normal tissues. Furthermore, concurrent usage of GL and bacteria in the treatment of induced 4T1 tumors in BALB/c mice significantly delayed tumor growth (p0.001) during 16 days of investigation. Based on these findings, BDEPT might be useful for targeted breast cancer therapy, although further investigations are required to confirm this.

Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities

Li, Fei,Wu, Si-Tong,Qu, Ming-Hui,Wang, Yi-Xiao,Ma, Chun-Liu,Yu, Bai-Hong,Wang, Guang-Shu

, (2021/07/17)

Three undescribed oleanane type triterpenoid saponins (1–3), along with one known saponin (4) were isolated from the whole herb of Hylomecon japonica. Their structures were elucidated by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HR-ESI-MS) and chromatographic date (GC and LC) as 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl ester (3), 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl ester (4). All saponins possess a partial sequence β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl at C-3 of the aglycon. Compound 1 has cytotoxic activity against human colon cancer cell lines HT29, 3 against human gastric cancer cell lines AGS, and 4 against human lung cancer cell lines A549, AGS and HT29. Among them, compounds 3 and 4 showed significant inhibitory effect against AGS with IC50 value of 6.01 ± 1.4 μM, 3.66 ± 1.8 μM, respectively. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon japonica and their bioactivities.

Bioactive oleanane-type saponins from Hylomecon Japonica

Li, Fei,Ma, Chun-Liu,Qu, Ming-Hui,Wang, Guang-Shu,Wang, Yi-Xiao,Wu, Si-Tong,Yu, Bai-Hong

, (2021/07/19)

Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.

A Reusable Column Method Using Glycopolymer-Functionalized Resins for Capture–Detection of Proteins and Escherichia coli

Ajish, Juby K.,Abraham, Hephziba Maria,Subramanian, Mahesh,Kumar, K. S. Ajish

, (2020/12/21)

The use of glycopolymer-functionalized resins (Resin–Glc), as a solid support, in?column mode for bacterial/protein capture and quantification is explored. The Resin–Glc is synthesized?from commercially available chloromethylated polystyrene?resin and glycopolymer, and is characterized by fourier transform infrared spectroscopy, thermogravimetry, and elemental analysis. The percentage of glycopolymer functionalized on Resin–Glc is accounted to be 5 wt%. The ability of Resin–Glc to selectively capture lectin, Concanavalin A, over Peanut Agglutinin, reversibly, is demonstrated for six cycles of experiments. The bacterial sequestration study using SYBR (Synergy Brands, Inc.) Green I tagged?Escherichia coli/Staphylococcus aureus?reveals the ability of Resin–Glc to selectively capture?E. coli?over?S. aureus. The quantification of captured cells in the column is carried out by enzymatic colorimetric assay using methylumbelliferyl glucuronide?as the substrate. The?E. coli?capture studies reveal a consistent capture efficiency of 105?CFU (Colony Forming Units) g?1 over six cycles. Studies with spiked tap water samples show satisfactory results for?E. coli?cell densities ranging from 102 to 107?CFU mL?1. The method portrayed can serve as a basis for the development of a reusable solid support in capture and detection of proteins and bacteria.

A novel acylated flavonol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica

Othman, Ahmed,Amen, Yhiya,Shimizu, Kuniyoshi

, (2021/05/17)

In recent years, the scientific interest and particularly the economic significance of halophytic plants has been highly demanding due to the medicinal and nutraceutical potential of its bioactive compounds. A xero-halophyte Bassia indica is deemed to be

Isolation and identification of two new sargentodoxosides from Sargentodoxa cuneata and their agonistic effects against FXR

Zhang, Wen,Sun, Cheng-Peng,Peng, Yu-Lin,Zhao, Wen-Yu,Wang, Zheng-Yue,Ning, Jing,Lv, Xia,Yu, Zhen-Long,Zhou, Shuang,Peng, Wei,Fang, Bang-Jiang,Ma, Xiao-Chi

, (2021/02/12)

Sargentodoxa cuneata (Oliv.) Rehd. et Wils is a traditional Chinese medicine to treat acute appendicitis, rheumarthritis, abdominal pain, and painful menstruation for a long history. The investigation of S. cuneata led to the isolation and identification of twenty-three secondary metabolites, including two new compounds, sargentodoxosides A (1) and B (2), and twenty-one known ones (3-23). Their structural characterization was conducted by HRESIMS, 1 D and 2 D NMR spectra. All the isolated compounds were assayed for their agonistic activities against the farnesoid X receptor (FXR). Nine of the isolated compounds displayed significant agonistic effects against FXR at 0.1 μM, suggesting that they could be served as potential agents for the development of FXR agonists.

Flavonol Glycosides from Leaves of Allium microdictyon

Olennikov

, p. 1035 - 1039 (2020/11/03)

The composition of flavonoids from leaves of Allium microdictyon Prokh. (Amaryllidaceae) was studied for the first time and included 14 compounds including two new flavonol glycosides 1 and 2. UV, IR, and NMR spectroscopic and mass spectrometric data dete

A immunosuppressive triterpenoid saponin from the stems of Epigynum griffithianum

Li, Wen-Yi,Wang, Qun,Wang, Yu-Dan

supporting information, p. 1389 - 1393 (2018/12/04)

Chemical investigation of the stems of Epigunum griffithianum led to the isolation and identification of a new triterpenoid saponin (1) and two known compounds (epigynosides A (2) and B (3)). These structures were elucidated by means of spectroscopic analysis (1D and 2D NMR, MS, UV, IR) as well as comparison with the reported data. Compound 1 was evaluated in vitro for the immunosuppressive activities on proliferation of mice splenocyte and displayed significant immunosuppressive activities compared to the positive control (dexamethasone) with the concentration at 25 μM. (Figure presented.).

Triterpene saponins from Silene gallica collected in North-Eastern Algeria

Bechkri, Sara,Alabdul Magid, Abdulmagid,Sayagh, Charlotte,Berrehal, Djemaa,Harakat, Dominique,Voutquenne-Nazabadioko, Laurence,Kabouche, Zahia,Kabouche, Ahmed

, (2020/01/25)

Eleven previously undescribed triterpene saponins, named silenegallisaponin A-K (1–11), were isolated from the aerial parts of Silene gallica L. Their structures were elucidated by analysis of 1D and 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). The saponins comprised caulophyllogenin, echinocystic acid, or quillaic acid substituted at C-3 by a β-D-glucuronic acid or β-D-galactopyranosyl-(1 → 3)-β-D-glucuronopyranoside and at C-28 by a β-D-fucopyranose substituted at C-2 by a β-D-glucose and at C-3 by a β-D-glucose or a β-D-quinovose.

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