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D(+)-Trehalose dihydrate

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CAS:6138-23-4
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D(+)-Trehalose dihydrate Basic information
Product Name:D(+)-Trehalose dihydrate
Synonyms:D-ALPHA,ALPHA-TREHALOSE DIHYDRATE;D(+)-TREHALOSE;D-(+)-TREHALOSE DIHYDRATE;D(+)TREHALOSE DIHYDRATE CELL*CULTURE TES TED;D(+)-TREHALOSE DIHYDRATE, FOR MICRO-BIOL OGY;.alpha.-D-Glucopyranoside, .alpha.-D-glucopyranosyl, dihydrate;d(+)-trehalose dihydrate, mycose;a,a-D-Trehaloseendotoxinfree
CAS:6138-23-4
MF:C12H22O11·2H2O
MW:378.33
EINECS:612-140-5
Product Categories:Basic Sugars (Mono & Oligosaccharides);Biochemistry;Disaccharides;Sugars;Dextrins、Sugar & Carbohydrates;Sugars, Carbohydrates & Glucosides
Mol File:6138-23-4.mol
D(+)-Trehalose dihydrate Structure
D(+)-Trehalose dihydrate Chemical Properties
Melting point 97-99 °C(lit.)
Boiling point 115.3 °C
alpha 179 º (c=2, H2O)
FEMA 4600 | TREHALOSE, DIHYDRATE
refractive index 181 ° (C=7, H2O)
storage temp. room temp
solubility H2O: 50 mg/mL
form powder
color White to Off-White
optical activity[α]20/D +179±3°, c = 2% in H2O
Water Solubility 68.9 g/100 mL (20 ºC)
Sensitive Hygroscopic
Merck 14,9580
BRN 5322018
InChIKeyDPVHGFAJLZWDOC-NYAOJISMSA-N
CAS DataBase Reference6138-23-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 38-36/37/38
Safety Statements 37/39-26-24/25
WGK Germany 2
RTECS LZ5776547
3-10
TSCA Yes
HS Code 29400000
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
D(+)-Trehalose dihydrate Usage And Synthesis
DescriptionTrehalose is a natural non-reducing disaccharide composed of two α-glucose units. It is found in all major groups of organisms except vertebrates, has biological functions as an osmolyte, storage reserve, and stress protectant, and has diverse commercial applications. Trehalose can also induce or enhance autophagy.
Chemical Propertieswhite to off-white crystalline powder
Chemical PropertiesD(+)-Trehalose dihydrate occurs as virtually odorless, white or almost white crystals with a sweet taste (approximately 45% of the sweetness of sucrose).
UsesD-(+)-Trehalose is a disaccharide composed of two α-glucose units. D-(+)-Trehalose is used in many processed foods as well as in biopharmaceutical monoclonal antibody formulations. D-(+)-Trehalose is also used as a protein stabilize.
UsesStabilizes cells during freezing, freeze-drying and air-drying. Sweetener and stabilizer in foods; cryoprotectant for freeze-dried foods. Additive in cosmetics and personal care products.
UsesAn osmolyte, chemical chaperone, and inducer of autophagy.D-(+)-Trehalose is a disaccharide composed of two α-glucose units. D-(+)-Trehalose is used in many processed foods as well as in biopharmaceutical monoclonal antibody formulations. D-(+)-Trehalose is also used as a protein stabilizer.
UsesFood additive; pharmaceutical excipient
Production MethodsTrehalose is prepared from liquefied starch by a multistep enzymatic process. The commercial product is the dihydrate.
General DescriptionTrehalose is a naturally occurring disaccharide which is used as a nontoxic cryoprotectant of enzymes, membranes and vaccines. It serves as a carbohydrate reserve in microorganisms and protects them from adverse conditions.
Pharmaceutical ApplicationsD(+)-Trehalose dihydrate is used for the lyoprotection of therapeutic proteins, particularly for parenteral administration. Other pharmaceutically relevant applications include use as an excipient for diagnostic assay tablets; for stabilization during the freeze–thaw and lyophilization of liposomes; and for stabilization of blood cells, cosmetics, and monoclonal antibodies. Trehalose may also be used in formulations for topical application.
Biochem/physiol ActionsTrehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond. It is thought to provide plants and animals with the ability to withstanding periods of dehydration.
SafetyTrehalose is used in cosmetics, foods, and parenteral and nonparenteral pharmaceutical formulations. It is generally regarded as a relatively nontoxic and nonirritant material when used as an excipient.
In the gut, trehalose is rapidly metabolized to glucose by the specific enzyme trehalase. A small minority of the population exhibits a primary (hereditary) or secondary (acquired) trehalase deficiency and thus may experience intestinal discomfort after ingestion of excessive amounts of trehalose owing to the osmotic activity of undigested trehalose in the gut. However, smaller amounts of trehalose are tolerated by such individuals without any symptoms.
Trehalose is used as a sweetener and is reported to have substantially less cariogenic potential than sucrose.
LD50 (dog, IV): >1 g/kg
LD50 (dog, oral): >5 g/kg
LD50 (mouse, IV): >1 g/kg
LD50 (mouse, oral): >5 g/kg
LD50 (rat, IV): >1 g/kg
LD50 (rat, oral): >5 g/kg
storageTrehalose is a relatively stable material. At 60°C for 5 hours it loses not more than 1.5% w/w of water (the dihydrate water of crystallization is retained). Open stored powder may liquefy at high relative humidity (≥90%).
Trehalose should be stored in a cool, dry place in a well-sealed container.
Purification Methodsα,α-D(+)-Trehalose crystallises (as the dihydrate) from aqueous EtOH. Dry it at 13o. For the anhydrous compound dissolve 10g in pyridine (200mL) and distil off this solvent at atmospheric pressure, and when the temperature rises to 115.3o all the H2O is removed and 73mL of distillate is collected. Most of the anhydrous material crystallises out at this stage. The crystals are collected (6.8g), washed with Et2O to give 6.1g of anhydrous product. Higher yields are obtained by slightly more prolonged distillation. [Birch J Chem Soc 3489 1965, X-ray cryst: Brown et al. Acta Cryst 28 3145 1972, Beilstein 17/8 V 3.]
IncompatibilitiesTrehalose is incompatible with strong oxidizing agents, especially in the presence of heat.
Regulatory StatusGRAS listed. In the UK trehalose may be used in certain food applications. Included in parenteral and nonparenteral investigational formulations.
D(+)-Trehalose dihydrate Preparation Products And Raw materials
Tag:D(+)-Trehalose dihydrate(6138-23-4) Related Product Information
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