ChemicalBook > CAS DataBase List > 6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE

6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE

Product Name: 6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE
CAS No.: 66758-35-8
Chemical Name: 6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE
Synonyms: 22:0 Trehalose;Trehalose Impurity;Trehalose-6,6'-dibehenate;Trehalose 6,6'-dibehenate;6,6'-dibehenoyl-α,α'-trehalose;D-(+)-trehalose 6,6'-dibehenate;6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE;6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE;D-(+)-TREHALOSE 6,6'-DIBEHENATE;22:0 TREHALOSE;α-D-Glucopyranoside, 6-O-(1-oxodocosyl)-α-D-glucopyranosyl, 6-docosanoate
CBNumber: CB0321080
Molecular Formula: C56H106O13
Formula Weight: 987.43
MOL File: 66758-35-8.mol

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6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE Property

Boiling point:: 945.8±65.0 °C(Predicted)
Density: 1.08±0.1 g/cm3(Predicted)
storage temp.: −20°C
solubility: DMF: Slightly Soluble
DMSO: Slightly Soluble
form: Solid
pka: 12.45±0.70(Predicted)
color: White to off-white
InChIKey: ZLJJDBSDZSZVTF-HYKPUQSJNA-N

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Biosynth Carbosynth

Product number: OT46136
Product name: Trehalose-6,6'-dibehenate
Packaging: 1mg
Price: $95
Updated: 2021/12/16

Biosynth Carbosynth

Product number: OT46136
Product name: Trehalose-6,6'-dibehenate
Packaging: 2mg
Price: $170
Updated: 2021/12/16

AK Scientific

Product number: 5251CS
Product name: Trehalose-6,6'-dibehenate
Packaging: 1mg
Price: $178
Updated: 2021/12/16

Biosynth Carbosynth

Product number: OT46136
Product name: Trehalose-6,6'-dibehenate
Packaging: 5mg
Price: $350
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CRB0003315
Product name: 6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE
Purity: 95.00%
Packaging: 5MG
Price: $498.05
Updated: 2021/12/16

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6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE Chemical Properties,Usage,Production

Uses

Trehalose-6,6'-dibehenate is an orally active glycolipid. Trehalose-6,6'-dibehenate activates Mincle and inflammasome, inducing IL-1β secretion in a caspase activity-dependent manner. Trehalose-6,6'-dibehenate exerts a Myd88-dependent adjuvant activity. Trehalose-6,6'-dibehenate induces Th-1/Th-17 immune responses[1][2][3][4][5].

Definition

ChEBI: Trehalose-6,6'-dibehenate is a fatty acid derivative and an O-acyl carbohydrate.

in vivo

Trehalose-6,6'-dibehenate (100 μg; i.p.; once) significantly reduced neutrophil recruitment in Nlrp3-deficient mice compared with wild-type mice in an in vivo inflammatory model experiment^[2].
Trehalose-6,6'-dibehenate (250 μg DDA liposomes + 50 μg TDB per dose; subcutaneous injection; 2-3 times; two weeks apart) induced a strong Th-1/Th-17 response in mice immunized with the fusion protein Ag85B-ESAT6, and its adjuvant activity was strictly dependent on Myd88^[3].
Trehalose-6,6'-dibehenate (present in DDA liposomes at different molar ratios (6.4-20 mol%); subcutaneous injection; 3 times; two weeks apart) was able to induce a strong and specific Th1-type immune response in female mice immunized with Ag85B-ESAT6, as evidenced by the production of a large amount of interferon-γ cytokine and high levels of IgG2b isotype antibodies^[4].
Trehalose-6,6'-dibehenate (10 mg/kg. p.o., once a day, 7 days) activates Mincle in mice^[5].

Animal Model:	Female C57BL/6j mice (8-12 weeks old), immunization model with Ag85B-ESAT6 (0.01 mg/ml)^[4]
Dosage:	DDA liposomes with different amounts of Trehalose-6,6'-dibehenate (TDB) (e.g., 250 μg DDA liposomes plus 25, 50 or 100 μg TDB per dose)
Administration:	Subcutaneous injection at the base of the tails three times, with a 2 - week interval between each immunization
Result:	Induced a strong, specific Th1-type immune response. Produced high levels of IFN-γ and low levels of IL-5. Elevated IgG2b antibody. Showed an IgG2b/IgG1 ratio characteristic of a Th1 immune response.

References

[1] Yu H, et, al. Chlamydia muridarum T-cell antigens formulated with the adjuvant DDA/TDB induce immunity against infection that correlates with a high frequency of gamma interferon (IFN-gamma)/tumor necrosis factor alpha and IFN-gamma/interleukin-17 double-positive CD4+ T cells. Infect Immun. 2010 May;78(5):2272-82. DOI:10.1128/IAI.01374-09
[2] Schweneker K, et al. The mycobacterial cord factor adjuvant analogue trehalose-6,6'-dibehenate (TDB) activates the Nlrp3 inflammasome. Immunobiology. 2013 Apr;218(4):664-73. DOI:10.1016/j.imbio.2012.07.029
[3] Althaus K. Mechanism of the adjuvant activity of the synthetic mycobacterial cord factor analog Trehalose-6, 6-dibehenate (TDB). Technische Universit?t München, 2010.
[4] Davidsen J, et al. Characterization of cationic liposomes based on dimethyldioctadecylammonium and synthetic cord factor from M. tuberculosis (trehalose 6,6'-dibehenate)-a novel adjuvant inducing both strong CMI and antibody responses. Biochim Biophys Acta. 2005 Dec 10;1718(1-2):22-31. DOI:10.1016/j.bbamem.2005.10.011
[5] Ruizhi T A N, et al. Chaihuang Yishen Granules Improves Renal Fibrosis in Mice with Chronic Kidney Disease by Inhibiting Macrophagic Mincle. Traditional Chinese Drug Research & Clinical Pharmacology, 2023: 1658-1667.
[6] ALEXANDRA HUBER. Trehalose diester glycolipids are superior to the monoesters in binding to Mincle, activation of macrophages in vitro and adjuvant activity in vivo.[J]. Innate Immunity, 2016, 22 6: 405-418. DOI: 10.1177/1753425916651132
[7] GÉRALD LARROUY-MAUMUS . Protective efficacy of a lipid antigen vaccine in a guinea pig model of tuberculosis[J]. Vaccine, 2017, 35 10: Pages 1395-1402. DOI: 10.1016/j.vaccine.2017.01.079

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View Lastest Price from 6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Trehalose-6,6'-dibehenate 66758-35-8
Price: US $0.00/G
Min. Order: 1G
Purity: 98%min
Supply Ability: 30kg/month
Release date: 2023-02-21

66758-35-8, 6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSERelated Search:

Trehalose DOCOSANOIC ACID ETHYL ESTER GLYCERYL MONOSTEARATE HENEICOSANOIC ACID-ETHYL ESTER POLYETHYLENE GLYCOL MONOSTEARATE 6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE MONOBEHENIN D(+)-Trehalose dihydrate DIETHYLENE GLYCOL MONOLAURATE Decanoyl/octanoyl-glycerides 1-MONOARACHIDIN 2-BUTOXYETHYL STEARATE

6,6'-dibehenoyl-α,α'-trehalose

6-O-(1-Oxodocosyl)-alpha-D-glucopyranosyl alpha-D-glucopyranoside 6-docosanoate

Trehalose 6,6'-dibehenate

22:0 Trehalose

D-(+)-TREHALOSE 6,6'-DIBEHENATE;22:0 TREHALOSE

α-D-Glucopyranoside, 6-O-(1-oxodocosyl)-α-D-glucopyranosyl, 6-docosanoate

((2R,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-6,6'-oxybis(3,4,5-trihydroxytetrahydro-2H-pyran-6,2-diyl))bis(methylene) didocosanoate

alpha-D-Glucopyranoside 6-O-(1-Oxodocosyl)-alpha-D-glucopyranosyl 6-Docosanoate

6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE

Trehalose-6,6'-dibehenate

((2R,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-Oxybis(3,4,5-trihydroxytetrahydro-2H-pyran-6,2-diyl))bis(methylene) didocosanoate

D-(+)-trehalose 6,6'-dibehenate

((2R,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-Oxybis(3,4,5-trihydroxytetrahydro-2H-pyran-6,2-diyl))bis(methylene) didocosanoate

6,6'-DIBEHENOYL-ALPHA,ALPHA'-TREHALOSE

Trehalose Impurity

66758-35-8

C56H106O13

Disaccharide

Biochemicals and Reagents

BioChemical

Carbohydrates