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Key Documents

T3034

Sigma-Aldrich

Trehalose 6,6′-dimycolate from Mycobacterium bovis

≥97% 6,6′-mycolate esters basis

Synonym(s):

6,6′-Di-O-mycoloyl-α,α-trehalose from Mycobacterium bovis, Cord factor from Mycobacterium bovis

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About This Item

CAS Number:
61512-20-7
MDL number:
MFCD00081533
UNSPSC Code:
12352201
NACRES:
NA.25

biological source

bacterial (Mycobacterium bovis)

assay

≥97% 6,6′-mycolate esters basis

form

powder

optical activity

[α]25/D 32 to 35 °, c = 1% (w/v) in chloroform/methanol/water (10:9:1)

storage temp.

−20°C

InChI

1S/C130H250O15/c1-5-9-13-17-21-25-29-33-37-41-43-45-47-49-51-53-57-61-65-71-81-89-97-105-117(131)116(104-96-88-80-74-73-78-86-94-102-114-108-112(114)100-92-84-76-68-63-59-55-40-36-32-28-24-20-16-12-8-4)128(140)142-110-120-122(134)124(136)126(138)130(144-120)145-129-125(137)123(135)121(133)119(143-129)109-141-127(139)115(103-95-87-79-70-64-60-56-52-50-48-46-44-42-38-34-30-26-22-18-14-10-6-2)118(132)106-98-90-82-72-66-69-77-85-93-101-113-107-111(113)99-91-83-75-67-62-58-54-39-35-31-27-23-19-15-11-7-3/h111-126,129-138H,5-110H2,1-4H3

InChI key

DJUMKUNMJWRLAX-UHFFFAOYSA-N

Biochem/physiol Actions

Cord factor is a glycolipid released from Mycobacterium that becomes toxic and antigenic when it interacts with cell surface lipids. It activates macrophages to release inflammatory cytokines and induces thymic atrophy and granuloma formation in lung and other organs. It is responsible for the necrosis and cavitation observed in secondary tuberculosis.

Other Notes

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC8936
BCCC4183
BCBZ9333
BCBW8173
BCBV6644

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Yasunobu Miyake et al.
Journal of immunology (Baltimore, Md. : 1950), 194(11), 5366-5374 (2015-04-19)
C-type lectin receptors expressed in APCs are recently defined pattern recognition receptors that play a crucial role in immune responses against pathogen-associated molecular patterns. Among pathogen-associated molecular patterns, cord factor (trehalose-6,6'-dimycolate [TDM]) is the most potent immunostimulatory component of the

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