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Key Documents

C8754

Sigma-Aldrich

Thiamine pyrophosphate

≥95%, powder

Synonym(s):

Aneurinepyrophosphoric acid, Cocarboxylase, Thiamine pyrophosphate chloride

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About This Item

Empirical Formula (Hill Notation):
C12H19ClN4O7P2S
CAS Number:
Molecular Weight:
460.77
Beilstein/REAXYS Number:
3875902
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.54

product name

Thiamine pyrophosphate, ≥95%

Quality Level

assay

≥95%

form

powder

solubility

H2O: soluble 50 mg/mL, clear to very slightly hazy, colorless

storage temp.

−20°C

SMILES string

CC1=C(CCOP(OP(O)(O)=O)(O)=O)SC=[N+]1CC2=C(N)N=C(C)N=C2.[Cl-]

InChI

1S/C12H18N4O7P2S.ClH/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21);1H

InChI key

YXVCLPJQTZXJLH-UHFFFAOYSA-N

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Application

Thiamine pyrophosphate from Sigma has been used as a substrate to assay the enzymes in golgi lamellae isolated from rat tissue.
Thiamine pyrophosphate has been used:
  • for the preparation of chitosan nano-particles
  • as a standard for vitamin B1 and its derivative in high-performance
  • liquid chromatography (HPLC) analysis
  • immunofluorescence

Biochem/physiol Actions

Thiamine pyrophosphate (TPP) is a coenzyme of transketolase, that catalyzes the cleavage of ribulose-5-phosphate. This reaction leads to the formation of D-glyceraldehyde-3-phosphate. It requires the addition of an acceptor aldehyde such as ribose-5-phosphate, glyceraldehye or glycolaldehyde. TPP is capable of decarboxylating hydroxypyruvate in the presence of an ′acceptor aldehyde′.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Thiamine pyrophosphate, a coenzyme of transketolase
Racker E, et al.
Journal of the American Chemical Society, 75(4), 1010-1011 (1953)
Nucleosidediphosphatase activity in the Golgi apparatus and its usefulness for cytological studies.
A B NOVIKOFF et al.
Proceedings of the National Academy of Sciences of the United States of America, 47, 802-810 (1961-06-15)
Immunofluorescence Analysis of Human Endocervical Tissue Explants Infected with Neisseria gonorrhoeae
Wang LC, et al.
Bio-protocol, 8(3) (2018)
Michael Moulin et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(36), 14622-14627 (2013-08-21)
Thiamin (vitamin B1) is an essential micronutrient needed as a cofactor for many central metabolic enzymes. Animals must have thiamin in their diet, whereas bacteria, fungi, and plants can biosynthesize it de novo from the condensation of a thiazole and
Enhancement of thiamine release during synthetic mutualism between Chlorella sorokiniana and Azospirillum brasilense growing under stress conditions
Palacios OA, et al.
Journal of Applied Phycology, 28(3), 1521-1531 (2016)

Articles

Explore thiamine's impact on serum-free cell culture systems for biomanufacturing monoclonal antibodies.

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