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’-Dibehenate Trehalose;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
- CBNumber:
- CB0321080
- Molecular Formula:
- C56H106O13
- Molecular Weight:
- 987.43
- MDL Number:
- MFCD00057968
- MOL File:
- 66758-35-8.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| pka | 12.45±0.70(Predicted) |
| form | Solid |
| color | White to off-white |
| Major Application | vaccine development |
| InChIKey | ZLJJDBSDZSZVTF-HYKPUQSJNA-N |
| SMILES | O[C@H]([C@@H](COC(CCCCCCCCCCCCCCCCCCCCC)=O)O[C@H](O[C@@H](O[C@@H]([C@H]([C@@H]1O)O)COC(CCCCCCCCCCCCCCCCCCCCC)=O)[C@@H]1O)[C@@H]2O)[C@@H]2O |
| FDA UNII | 672NB7JH7R |
| UNSPSC Code | 12352211 |
| NACRES | NA.25 |
6,6'-Dibehenoyl-alpha,alpha'-trehalose price More Price(27)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 37911 | Trehalose 6,6''-Dibehenate ≥95% | 66758-35-8 | 1mg | $47 | 2026-04-30 | Buy |
| Cayman Chemical | 37911 | Trehalose 6,6''-Dibehenate ≥95% | 66758-35-8 | 5mg | $208 | 2026-04-30 | Buy |
| Cayman Chemical | 37911 | Trehalose 6,6''-Dibehenate ≥95% | 66758-35-8 | 10mg | $347 | 2026-04-30 | Buy |
| Cayman Chemical | 37911 | Trehalose 6,6''-Dibehenate ≥95% | 66758-35-8 | 25mg | $578 | 2026-04-30 | Buy |
| Biosynth | OT46136 | Trehalose-6,6'-dibehenate | 66758-35-8 | 1mg | $172.34 | 2026-06-04 | Buy |
6,6'-Dibehenoyl-alpha,alpha'-trehalose Chemical Properties,Uses,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 Universitt 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
6,6'-Dibehenoyl-alpha,alpha'-trehalose Preparation Products And Raw materials
Raw materials
Preparation Products
6,6'-Dibehenoyl-alpha,alpha'-trehalose Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Jinan Samuel Pharmaceutical Co., Ltd. | 0531-88821801 15192360884 | 605818151@qq.com | China | 479 | 58 |
| Daicel Chiral Technologies (China)CO.,LTD | 021-50460086-9 15921403865 | han_yajun@dctc.daicel.com | China | 7909 | 65 |
| Shanghai Aladdin Bio-Chem Technology Co.,LTD | 400-6206333 13167063860 | anhua.mao@aladdin-e.com | China | 29985 | 65 |
| Bide Pharmatech Ltd. | 400-164-7117 18317119277 | product02@bidepharm.com | China | 40000 | 60 |
| Quality Control Solutions Ltd. | 0755-66853366 13670046396 | orders@qcsrm.com | China | 18188 | 56 |
| Shanghai Haozhixiang Biotechnology Co., Ltd | 526763801 13301653310 | 526763801@qq.com | China | 7580 | 55 |
| Shanghai Qiao Chemical Science Co., Ltd | 021-58892003 | info@qiaochem.com | China | 6065 | 65 |
| Shanghai YuanYe Biotechnology Co., Ltd. | 15026964105 | 2881489226@qq.com | China | 89667 | 60 |
| Chengdu Huachun Technology Co., Ltd | 400-1166-196 15982826727 | cdhxsj@163.com | China | 14571 | 60 |
| Zhengzhou Huiju Chemical Co., Ltd. | 0371-55900031 18137872243 | 3927209986@qq.com | China | 9997 | 55 |
View Lastest Price from 6,6'-Dibehenoyl-alpha,alpha'-trehalose manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-09-11 | Trehalose-6,6'-dibehenate
66758-35-8
|
1G | 98%min | 30kg/month | WUHAN FORTUNA CHEMICAL CO., LTD |
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- Trehalose-6,6'-dibehenate
66758-35-8
- $0.00
- 98%min
- WUHAN FORTUNA CHEMICAL CO., LTD
