Trehalose

HCID 7427
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Basic information

CAS
99-20-7
Standard SMILES
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
InChIKey
HDTRYLNUVZCQOY-LIZSDCNHSA-N
Molecular formula
C12H22O11
Average molar mass
342.3 g/mol
Monoisotopic mass
342.11621152

Overview

Alpha,alpha-trehalose is a trehalose in which both glucose residues have alpha-configuration at the anomeric carbon. It has a role as a geroprotector, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite.

Names & identifiers

Preferred name
Trehalose
IUPAC
(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
English name
Trehalose
Molecular formula
C12H22O11
Molecular weight
342.3

Names & synonyms

trehalose99-20-7D-(+)-TrehaloseMycosealpha,alpha-trehaloseErgot sugaralpha-D-TrehaloseCabalettaMushroom sugarNatural trehalosealpha-D-glucopyranosyl-alpha-D-glucopyranosidealpha,alpha'-Trehalose
Show more names
α,α-trehaloseD-TREHALOSEalpha-d-glucopyranosideTrehalose RSalpha-TrehaloseTrehalose solution
alpha-D-glucopyranosyl alpha-D-glucopyranosideCHEBI:16551B8WCK70T7INSC-2093(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(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triolCHEBI:27082(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxane-3,4,5-triol

Database identifiers

CAS
99-20-7
PubChem CID
7427
DTXSID
DTXSID3048102
ChEMBL
CHEMBL1236395
ChEBI
CHEBI:16551
UNII
B8WCK70T7I
EC Number
202-739-6
Nikkaji
J4.965D

Properties

Computed structural properties

XLogP
-4.2
Topological polar surface area
190 Ų
Hydrogen bond donors
8
Hydrogen bond acceptors
11
Rotatable bonds
4
Heavy atoms
23

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Disaccharides
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 2 items

Cosmetic ingredients (Trehalose) -> CIR (Cosmetic Ingredient Review)

Humectant; Moisturising

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point203 °C
Physical Description · 2 items

Dihydrate: Solid; [Merck Index] White or nearly white solid; [JECFA] White crystalline powder; [Acros Organics MSDS]

Solid

Physicochemical properties

Melting point
203 °C · 203 °C
Boiling point
397.76 °C · 397.76°C (rough estimate)
Density
1.58 · 1.5800
vapor pressure
0.001 Pa · 0.001Pa at 25℃
refractive index
197 ° · 197 ° (C=7, H2O)
RTECS
5776770 · LZ5776770

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 99.8% (429 of 430) of all reports.

Not Classified

Aggregated GHS information provided per 430 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: .alpha.-D-Glucopyranoside, .alpha.-D-glucopyranosyl

Status: Active Update: 02-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/26864

.alpha.-D-Glucopyranoside, .alpha.-D-glucopyranosyl: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryNot toxic or mutagenic in subchronic toxicity studies; [ToxPlanet: Health Council of the Netherlands] The dihydrate is the product of commerce (CAS# 6138-23-4); [JECFA] May cause irritation; [Acros Organics MSDS]
Hazard Classes and CategoriesNot Classified

Toxicology

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

Safety data

wgk
WGK 1
tsca
TSCA listed
hs_code
29400090
risk_code
38
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

Tissue LocationsEpidermis
Cellular LocationsExtracellular
Metabolite PathwaysTrehalose Degradation

Uses & manufacturing

Uses · 2 items

CIR ingredient: Trehalose

Disaccharide present in fungi, bacteria, yeasts, and insects; Used to stabilize cells during freeze-drying and air-drying, as a sweetener and stabilizer in foods, and as an additive in cosmetics; [Merck Index] Used as a texturizer, stabilizer, humectant, and sweetener in foods; [JECFA]

Household ProductsInformation on 31 consumer products that contain Trehalose in the following categories is provided:
Use Classification · 3 items

Food Additives -> HUMECTANT; STABILIZER; SWEETENER; TEXTURIZER; THICKENER -> JECFA Functional Classes

Food Additives -> HUMECTANT; STABILIZER; SWEETENER; TEXTURIZER; THICKENER -> JECFA Functional Classes

Cosmetics -> Humectant; Moisturising

General Manufacturing Information.alpha.-D-Glucopyranoside, .alpha.-D-glucopyranosyl: ACTIVE
Applications · 3 items

DescriptionTrehalose is a nonreducing disaccharide in which the two glucose molecules are linked together in an α,α-1,1-glycosidic linkage. α,α-trehalose is the only anomer of trehalose, which has been isolated from and biosynthesized in living organisms. This sugar is present in a wide variety of organisms, including bacteria, yeast, fungi, insects, invertebrates, and lower and higher plants, where it may serve as a source of energy and carbon. It can be used as a stabilizer and protectant of proteins and membranes: protection from dehydration; protection from damage by oxygen radicals (against oxidation); protection from cold; as a sensing compound and/or growth regulator; as a structural component of the bacterial cell wall. Trehalose is used in the biopharmaceutical preservation of labile protein drugs and in the cryopreservation of human cells. It is used as an ingredient for dried and processed food, and as an artificial sweetener, with a relative sweetness of 40-45% that of sucrose. Several safety studies on trehalose have been evaluated by JECFA, 2001 and allocated an ADI of ‘not specified’. Trehalose is approved in Japan, Korea, Taiwan, and UK. Trehalose could be possibly used in an eye drop solution to against corneal damage due to desiccation (dry eye syndrome).

Usestrehalose is a humectant and moisturizer, it helps bind water in the skin and increase the skin’s moisture content. It is a naturally occurring plant sugar.

UsesD-(+)-Trehalose can be used for the effects of sucrose on blood avidity in mosquitoes.

Upstream & downstream products

Upstream raw materials

Downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.

Related reactions

40 records
New reaction record

Compound notes

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