1,6-Anhydro-β-D-glucose - 10mM in DMSO , CAS No.498-07-7

CAS: 498-07-7 Cat. No.: A424290 Molecular Weight: 162.14 Beilstein Registry Number: 80998 EC Number: 207-855-0

GRADE & PURITY 10mM in DMSO

Synonyms

1,6-ANHYDRO-D-GLUCOSE [USP-RS] | 1,6-Anhydro-b-D-glucopyranose | 1,6-Anhydro-b-D-glucose | Anhydro-d-mannosan | 1,6-Anhydro-beta-delta-glucopyranose | 1,6-Anhydro-beta-glucopyranose | A827859 | 4PW | 6,8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

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.

Specifications

Synonyms

1, 6-ANHYDRO-D-GLUCOSE [USP-RS] | 1, 6-Anhydro-b-D-glucopyranose | 1, 6-Anhydro-b-D-glucose | Anhydro-d-mannosan | 1, 6-Anhydro-beta-delta-glucopyranose | 1, 6-Anhydro-beta-glucopyranose | A827859 | 4PW | 6, 8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C1C2C(C(C(C(O1)O2)O)O)O
• IUPAC Name: (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• InChIKey: TWNIBLMWSKIRAT-VFUOTHLCSA-N
• 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
• 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=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Oxepanes

• 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

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

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

References

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).  [PMID:36874944] [10.1039/D2RA07419B]

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,      [PMID:] [10.1016/j.jaap.2022.105663]

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).  [PMID:] [10.1039/C9GC03066B]

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,      [PMID:] [10.1021/acs.energyfuels.9b02863]

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,      [PMID:] [10.1016/j.biombioe.2015.03.025]

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).  [PMID:38265079] [10.1039/D3DT04000C]

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,      [PMID:39846727] [10.1021/acs.jafc.4c10378]

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,      [PMID:] [10.1016/j.fuel.2025.135136]

9. Hong-li Ma, Ming-fu Li, Ying-chuan Zhang, Qing-hua Huang, Li-qun Jiang, Zhen Fang.  (2025)  Nearly 100% selective hydrolysis of pyrolytic sugar over sustainable carbon catalysts enables highly efficient production of bioethanol.  BIORESOURCE TECHNOLOGY,      [PMID:40683473] [10.1016/j.biortech.2025.133008]