Trehalose dihydrate

Catalog Number	ACM6138234-4
CAS	6138-23-4
Structure
Synonyms	D(+)-Trehalose dihydrate
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
Molecular Weight	378.33
Molecular Formula	C12H26O13
Canonical SMILES	C(C1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O.O.O
InChI	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
InChI Key	DPVHGFAJLZWDOC-PVXXTIHASA-N
Melting Point	97-99 °C
Purity	98%+
Complexity	348
Covalently-Bonded Unit Count	3
Defined Atom Stereocenter Count	10
Exact Mass	378.13734088
Heavy Atom Count	25
Hydrogen Bond Acceptor Count	13
Hydrogen Bond Donor Count	10
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
Monoisotopic Mass	378.13734088
Physical State	Powder
Rotatable Bond Count	4
Topological Polar Surface Area	192 Ų

Knowledge & Learning Case Study Q&A

Trehalose as A Superior Cryoprotectant for Enhancing Protein Stability

Olsson C, et al. J. Phys. Chem. B, 2016, 120, 20, 4723-4731.

Cells and tissues are preserved at low temperatures. To avoid freezing, most of the water molecules in the sample must be replaced by cryoprotectants.
Disaccharide trehalose with its high Tg and excellent ability to prevent water crystallization can be used as a cryoprotectant. It also has a high rate of recovery of protein function after cryopreservation and an excellent ability to protect the lipid bilayer at low and high temperatures or under dehydration.
The mechanism of protection is as follows:
The protein molecules are preferentially hydrated, as evidenced by the fact that there are usually one or two molecular layers of water on the surface of the protein. Trehalose forms structures close to the surface of the protein and these form multiple hydrogen bonds (HB) with the water layer on the protein surface. The trehalose molecules and the remaining water molecules are distributed almost randomly between the hydrated protein molecules.
As a result, protein dynamics are associated with more rigid trehalose-water structures through the water layer, which slows down protein dynamics and increases protein stability.

Trehalose for the Synthesis of 3HC Solvatochromic Dyes Conjugate

Kamariza M, et al. JACS Au, 2021, 1(9), 1368-1379.

Trehalose can be used to synthesize a bright solvatochromic 3-hydroxychromone (3HC) dye conjugate of trehalose (3HC-3-Tre) that can specifically detect Mycobacterium tuberculosis within minutes.
Synthesis of 6-Br-Ac7-Tre:
An Appel reaction using N-bromosuccinimide and triphenylphosphine resulted in a mixture of monobrominated target compound (6-Br-Tre), a dibrominated side product (6,6'-dibromo-6,6'-dideoxy-α,α'-trehalose) and unreacted starting material. The crude material is then acetylated and purified to give 6-Br-Ac7-Tre.
Synthesis of the Aldehyde Precursor to 3HC-3
Nitrate 2-bromo-9,9-dimethylfluorene at the 7-position, reduce the nitrate to an amine, alkylate the amine using ethyl iodide, and convert the bromine to an aldehyde through a Bouveault reaction. To form 3HC-3, the aldehyde is reacted with 2'-hydroxyacetophenone and then treated with hydrogen peroxide to obtain the desired products.
Synthesis of Dye-Tre Probes:
The aromatic hydroxyl group on the dye is deprotonated with potassium carbonate and used to displace the bromine atom on 6-Br-Ac7-Tre. The crude dye-Ac7-Tre is then deacetylated with catalytic sodium methoxide and purified to produce the final dye-Tre products.

Trehalose Dihydrate as a Superior Spray-Drying Excipient for Liposome Preservation

Lutta A, et al. International Journal of Pharmaceutics, 2024, 652, 123798.

Trehalose has been recognized as the optimal spray-drying excipient for protecting liposomes and is extensively used to safeguard biologics during the drying process. This case study explores the use of a mixture of trehalose dihydrate and dextran as a precursor for spray-drying CAF04 liposomes. The experimental procedure is as follows:
1. Preparation of Liposome Dispersions:
Liposome dispersions are created using the thin film hydration method. N,N-dimethyl-N,N-dioctadecylammonium bromide (DDA) and monomycoloyl glycerol (MMG) lipid powders are weighed in a 5:1 weight ratio and dissolved in 99% ethanol. The lipid film is formed by evaporating the ethanol overnight, followed by nitrogen flushing to remove any residue.
2. Rehydration of Lipid Film:
The lipid film is rehydrated in milliQ water containing either trehalose dihydrate or a mixture of trehalose dihydrate and dextran. High-shear mixing is used to prepare the liposomes at 21,000 rpm for 15 minutes at 60℃ with a universal laboratory homogenizer.
3. Spray Drying:
The liposome dispersions are spray-dried using a miniature spray dryer with air as the drying gas. The dry particles are separated from the gas stream by centrifugal force utilizing a high-performance cyclone.
4. Determination of Dry Powder Yield:
The dry powder yield is measured by determining the weight difference of the collection vessel before and after spray drying. This weight difference is compared to the initial total dry mass in the feed, and the yield is calculated. The resulting powder is stored in airtight glass bottles at -20℃ until further use.
It is demonstrated that trehalose dihydrate fortified with small amounts of dextran adequately protects CAF04 liposomes during spray drying.

What is the product name of the compound with CAS number 6138-23-4?

The product name is Trehalose dihydrate.

What is the molecular weight of Trehalose dihydrate?

The molecular weight is 378.33.

What is the molecular formula of Trehalose dihydrate?

The molecular formula is C12H26O13.

What is the melting point of Trehalose dihydrate?

The melting point is 97-99 °C.

What is the purity level of Trehalose dihydrate?

The purity is 98%+.

What is the physical state of Trehalose dihydrate?

It is in the form of powder.

What are some synonyms of Trehalose dihydrate?

Some synonyms include D(+)-Trehalose dihydrate.

What are the typical applications of Trehalose dihydrate?

It is used as an emulsion stabilizer and dispersing agent.

What is the IUPAC name of Trehalose dihydrate?

The IUPAC name 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;dihydrate.

What is the InChI Key of Trehalose dihydrate?

The InChI Key is DPVHGFAJLZWDOC-PVXXTIHASA-N.

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