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Basic Description
| Synonyms | Levoglucosan | 498-07-7 | 1,6-Anhydro-beta-D-glucopyranose | Leucoglucosan | 1,6-Anhydro-beta-D-glucose | 1,6-Anhydro-beta-glucopyranose | 1,6-Anhydroglucose | Glucosan | (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol | 1,6-Anhydro-D-glucose | 1,6-Anhydro-b-D-glu |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products such as rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, macrolide antibiotics and modified sugars. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Organoheterocyclic compounds
- Class Oxepanes
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Superclass
Organoheterocyclic compounds
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Oxepanes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Oxepanes |
| Alternative Parents | Oxanes Monosaccharides 1,3-dioxolanes Secondary alcohols Polyols Oxacyclic compounds Acetals Hydrocarbon derivatives |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Oxepane - Oxane - Monosaccharide - Meta-dioxolane - Secondary alcohol - Oxacycle - Polyol - Acetal - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as oxepanes. These are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. |
| External Descriptors | anhydrohexose |
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Associated Targets(Human)
SLCO1B1
Tchem
Solute carrier organic anion transporter family member 1B1 (2672 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Names and Identifiers
| IUPAC Name | (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol |
|---|---|
| INCHI | InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1 |
| InChIKey | TWNIBLMWSKIRAT-VFUOTHLCSA-N |
| Smiles | C1C2C(C(C(C(O1)O2)O)O)O |
| Isomeric SMILES | C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)O)O)O |
| WGK Germany | 3 |
| Molecular Weight | 162.14 |
| Beilstein | 80998 |
| Reaxy-Rn | 10784442 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10784442&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Specific Rotation[α] | -66.5 ° (C=2, H2O) |
|---|---|
| Melt Point(°C) | 182-184°C |
| Molecular Weight | 162.140 g/mol |
| XLogP3 | -2.100 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Exact Mass | 162.053 Da |
| Monoisotopic Mass | 162.053 Da |
| Topological Polar Surface Area | 79.200 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 161.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Citations of This Product
| 1. Xiunan Yao, Ninglian Wang, Xingwang Zheng, Quanlian Li, Ewerton Santos, Linda Maharjan, Junjie Wang, Zhihui Guo, Jiahua Guo, Huan Zhang, Kui Zheng, Jingquan Wu, Yao Li. (2023) Highly sensitive ultra-performance liquid chromatography coupled with triple quadrupole mass spectrometry detection method for levoglucosan based on Na+ enhancing its ionization efficiency. RSC Advances, 13 (10): (7030-7036). |
| 2. Haoran Yuan, Chengyu Li, Rui Shan, Jun Zhang, Lingjun Zhu, Yong Chen. (2022) Municipal sludge derived solid acids for levoglucosenone production via cellulose fast pyrolysis. JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 167 (105663). |
| 3. Yan Wan, Lina Zhang, Yeyun Chen, Jinhan Lin, Wenda Hu, Shuai Wang, Jingdong Lin, Shaolong Wan, Yong Wang. (2019) One-pot synthesis of gluconic acid from biomass-derived levoglucosan using a Au/Cs2.5H0.5PW12O40 catalyst. GREEN CHEMISTRY, 21 (23): (6318-6325). |
| 4. Yuan Zhao, Kaifeng Lu, Hao Xu, Yang Qu, Lingjun Zhu, Shurong Wang. (2019) Comparative Study on the Dehydration of Biomass-Derived Disaccharides and Polysaccharides to 5-Hydroxymethylfurfural. ENERGY & FUELS, 33 (10): (9985–9995). |
| 5. Wei Lv, Qi Zhang, Chenguang Wang, Tiejun Wang, Jinxing Long, Ying Xu, Longlong Ma. (2015) Interaction among bio-oil model components during oxidative degradation. BIOMASS & BIOENERGY, 77 (135). |
| 6. Mingfu Li, Liqun Jiang, Sufei Feng, Junsheng Huang, Pingjun Zhang, Jian Zhang. (2024) Aluminum ion intercalation in mesoporous multilayer carbocatalysts promotes the conversion of glucose to 5-hydroxymethylfurfural. DALTON TRANSACTIONS, 53 (7): (3386-3396). |
| 7. Shuang Lu, Zhengxiong Tao, Gan Wang, Kai Na, Lisha Wu, Li Zhang, Xiangyu Li, Xiaohua Guo. (2025) Mannuronate Oligosaccharides Ameliorate Experimental Colitis and Secondary Neurological Dysfunction by Manipulating the Gut–Brain Axis. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 73 (5): (2935-2950). |
| 8. Jie Wang, Quanxing Zheng, Hongliang Lu, Jianqiang Fan, Xiaohua Deng, Wenjing Song, Pengfei Ma, Weikun Lai. (2025) TiO2 layer coated MoO3 nanorod supported Ni catalyst for selective hydrogenolysis of cellulose to ketones and alcohols. FUEL, 394 (135136). |
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