D-(+)-Trehalose dihydrate - 10mM in DMSO , CAS No.6138-23-4

CAS: 6138-23-4 Cat. No.: D425084 Formula: C₁₂H₂₂O₁₁·2H₂O Molecular Weight: 378.33 Beilstein Registry Number: 5322018 EC Number: 612-140-5

GRADE & PURITY 10mM in DMSO

Synonyms

D-(+)-Trehalose dihydrate|6138-23-4|Trehalose dihydrate|D-Trehalose dihydrate|alpha,alpha-Trehalose dihydrate|TREHALOSE, DIHYDRATE|7YIN7J07X4|DTXSID3047972|MFCD00071594|(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymeth

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Trehalose, Dihydrate, is an osmolyte, a chemical chaperone and inducer of autophagy, that has been reported to protect cells against numerous environmental stresses. This compound contains many properties that allow it to stabilize partially unfolded protein molecules and inhibit protein aggregation. These properties include a low chemical reactivity, high glass transition temperature, existence of numerous polymorphs, nonreducing nature, and high affinity for water molecules. Additionally, Trehalose has been noted to bind to expanded polyglutamines and stabilize partially unfolded polyglutamine-containing proteins.
An osmolyte, chemical chaperone, and inducer of autophagy.

Specifications

Synonyms

D-(+)-Trehalose dihydrate | 6138-23-4 | Trehalose dihydrate | D-Trehalose dihydrate | alpha,alpha-Trehalose dihydrate | TREHALOSE, DIHYDRATE | 7YIN7J07X4 | DTXSID3047972 | MFCD00071594 | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymeth

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Biochem/physiol Actions：D-(+)-Trehalose shows anti-desiccant and cryopreservative activities. It acts as an osmolyte, and stress protectant and helps in the storage and transport of carbon. Trehalose is involved in the food, cosmetic, and pharmaceutical i

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

Pubchem Sid

528763984

Canonical Smiles

[H]O[H].[H]O[H].OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

IUPAC Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol;dihydrate

InChIKey

DPVHGFAJLZWDOC-PVXXTIHASA-N

INCHI

1S/C12H22O11.2H2O/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12;;/h3-20H,1-2H2;2*1H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-;;/m1../s1

Isomeric SMILES

C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)O.O.O

WGK Germany

2

Molecular Weight

378.33

Beilstein

5322018

Reaxy-Rn

5322018

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5322018&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 O-glycosyl compounds

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: O-glycosyl compounds
• Alternative Parents: Disaccharides Oxanes Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: O-glycosyl compound - Disaccharide - Oxane - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Polyol - Acetal - Organic oxide - Hydrocarbon derivative - Primary alcohol - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
• External Descriptors: Not available

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Hygroscopic.
• Specific Rotation[α]: 181 ° (C=7, H2O)
• Melt Point(°C): 97-99°C
• Molecular Weight: 378.330 g/mol
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 4
• Exact Mass: 378.137 Da
• Monoisotopic Mass: 378.137 Da
• Topological Polar Surface Area: 192.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 348.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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: 3

XLogP3