Trehalose

Catalog Number	ACM99207-3
CAS	99-20-7
Structure
Synonyms	D-Trehaloseanhydrous
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
Molecular Weight	342.3
Molecular Formula	C12H22O11
Canonical SMILES	C(C1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O
InChI	InChI=1S/C12H22O11/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/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
InChI Key	HDTRYLNUVZCQOY-LIZSDCNHSA-N
Boiling Point	397.76 °C
Melting Point	203 °C
Flash Point	362.3 °C
Purity	98%
Density	1.5800 g/cm³
Solubility	Soluble in water
Appearance	White to off-white powder
Storage	Inert atmosphere, room temperature
Complexity	348
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	10
EC Number	202-739-6
Exact Mass	342.11621151
Heavy Atom Count	23
Hydrogen Bond Acceptor Count	11
Hydrogen Bond Donor Count	8
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
Monoisotopic Mass	342.11621151
Physical State	Powder
Rotatable Bond Count	4
Shipping	Ambient temperature
Storage Conditions	Inert atmosphere,Room Temperature
Topological Polar Surface Area	190 Ų

Knowledge & Learning Case Study Q&A

Trehalose as a Key Mediator in Salinity-Stress Tolerance of Freshwater Organisms

Santos JL, et al. Current Biology, 2024.

Trehalose plays a pivotal role in salinity-stress tolerance in a variety of organisms, ranging from bacteria to plants and invertebrates. Recent studies have shown that this sugar is integral to the adaptation mechanisms of Daphnia magna, a freshwater crustacean exposed to increasing salinity levels. This case study investigates the function of trehalose in facilitating salinity tolerance through both local adaptation and phenotypic plasticity in D. magna populations.
The critical gene involved in trehalose biosynthesis, Alpha,alpha-trehalose-phosphate synthase (TPS), has been identified as a major determinant of salinity tolerance. Genomic studies reveal that the ability of D. magna to withstand elevated salinity is highly correlated with the functionality of the TPS gene, which facilitates the production of trehalose. Salinity-tolerant genotypes express this gene and synthesize trehalose in response to osmotic stress, whereas intolerant genotypes with a non-functional TPS gene fail to produce trehalose and thus, cannot survive under high-salinity conditions. The production of trehalose is energetically expensive but offers a protective mechanism by stabilizing proteins and cell membranes, mitigating the detrimental effects of hyperosmotic environments.
The study also highlights the gene-environment interactions that underpin salinity tolerance. Genetic variants in D. magna demonstrate a clear pattern of local adaptation, where genotypes from saline habitats produce trehalose under stress, while those from low-salinity environments do not. This adaptability is essential for their survival amidst changing environmental conditions.

Therapeutic Potential of Trehalose in Treating Spinocerebellar Ataxia Type 3

Wang Z, et al. Neuroscience, 2024, 555, 76-82.

Recent studies have explored the potential of alginate for the treatment of Spinocerebellar Ataxia Type 3 (SCA3), a neurodegenerative disorder caused by the aggregation of mutant ataxin 3 with abnormally expanded polyglutamine (polyQ) bundles.
Trehalose is known to induce autophagy, a cellular defense mechanism against the toxic effects of aggregation-prone misfolded proteins, making it a candidate for addressing neurodegenerative diseases like SCA3. In an SCA3 cell model utilizing HEK293T cells overexpressing ataxin-3-15Q or ataxin-3-77Q, trehalose demonstrated significant therapeutic effects. At safe concentrations ranging from 0.1 to 200 mM, trehalose effectively reduced the formation of aggregates of mutant ataxin-3, as evidenced by filter trap assay results. Furthermore, Western blot analysis showed that trehalose reduced the overall levels of full-length ataxin-3 protein, which is crucial in mitigating the cytotoxic effects caused by the accumulation of these mutant proteins.
Beyond its role in promoting autophagy, trehalose appears to exhibit antioxidant properties. The reduction in soluble ataxin-3 protein levels and the observed neuroprotective effects against oxidative stress suggest that trehalose's therapeutic potential may be partly due to its antioxidative activity. Total antioxidant capacity assays further support this hypothesis.

What is the molecular formula of trehalose?

The molecular formula of trehalose is C12H22O11.

What is the molecular weight of trehalose?

The molecular weight of trehalose is 342.30 g/mol.

What is the IUPAC name of trehalose?

The IUPAC name of trehalose is (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.

Is trehalose used as a metabolite by Escherichia coli?

Yes, trehalose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

What is the InChIKey of trehalose?

The InChIKey of trehalose is HDTRYLNUVZCQOY-LIZSDCNHSA-N.

How many hydrogen bond donor counts does trehalose have?

Trehalose has 8 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does trehalose have?

Trehalose has 11 hydrogen bond acceptor counts.

What is the XLogP3-AA value of trehalose?

The XLogP3-AA value of trehalose is -4.2.

What is the CAS number of trehalose?

The CAS number of trehalose is 99-20-7.

What is the exact mass of trehalose?

The exact mass of trehalose is 342.11621151 g/mol.

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