A synthetic glycolipid and derivative of TDM
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Trehalose 6,6'-Dibehenate

Item No. 37911

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-docosanoate 6-O-(1-oxodocosyl)-α-D-glucopyranosyl α-D-glucopyranoside
CAS Number
66758-35-8
Synonyms
  • TDB
  • Trehalose Dibehenate
  • 22:0 Trehalose
Molecular Formula
C56H106O13
Formula Weight
987.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly SolubleDMSO: Slightly Soluble
SMILES
O[C@H]([C@H]1O)[C@H](O[C@@H]([C@H]1O)COC(CCCCCCCCCCCCCCCCCCCCC)=O)O[C@H]([C@@H]([C@H]2O)O)O[C@@H]([C@H]2O)COC(CCCCCCCCCCCCCCCCCCCCC)=O
InChi Code
InChI=1S/C56H106O13/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-47(57)65-43-45-49(59)51(61)53(63)55(67-45)69-56-54(64)52(62)50(60)46(68-56)44-66-48(58)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h45-46,49-56,59-64H,3-44H2,1-2H3/t45-,46-,49-,50-,51+,52+,53-,54-,55-,56-/m1/s1
InChi Key
ZLJJDBSDZSZVTF-LXOQPCSCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $47

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    5 mg

    $208

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    10 mg

    $347

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    25 mg

    $578

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    Cayman Chemical
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    Product Description

    Trehalose 6,6'-dibehenate (TDB) is a synthetic glycolipid and derivative of trehalose-6,6′ dimycolate (TDM), also known as mycobacterial cord factor.1 It binds to a fusion protein of mouse macrophage-inducible C-type lectin (Mincle) and human IgG1 Fc in a cell-free assay when used at a concentration of 10 µg/ml. TDB (5 µg/ml) induces nitric oxide (NO) and G-CSF production in mouse bone marrow macrophages in a Mincle-dependent manner. Liposomes containing TDB and dimethyldioctadecylammonium (DDA; Item No. 26120) as adjuvants and the mycobacterial lipid antigens diacylated sulfoglycolipid (Ac2SGL) and phosphatidyl-myo-inositol dimannoside (PIM2) decrease spleen bacterial load and the number of lung and spleen lesions in a guinea pig model of M. tuberculosis infection.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huber, A., Kallerup, R.S., Korsholm, K.S., et al. Trehalose diester glycolipids are superior to the monoesters in binding to Mincle, activation of macrophages in vitro and adjuvant activity in vivo. Innate Immun. 22(6), 405-418 (2016).

    2. Larrouy-Maumus, G., Layre, F., Clark, S., et al. Protective efficacy of a lipid antigen vaccine in a guinea pig model of tuberculosis. Vaccine 35(10), 1395-1402 (2017).