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64255

Sigma-Aldrich

Methylenediphosphonic acid

for molecular studies & mass spectrometry

Synonym(s):

MDP, Medronic acid

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About This Item

Linear Formula:
CH2[P(O)(OH)2]2
CAS Number:
1984-15-2
Molecular Weight:
176.00
Beilstein:
1708494
MDL number:
MFCD00002139
UNSPSC Code:
12352106
PubChem Substance ID:
57651976
NACRES:
NA.52

Quality Level

200

form

powder

mp

197-199 °C (lit.)
201-205 °C

storage temp.

2-8°C

SMILES string

OP(O)(=O)CP(O)(O)=O

InChI

1S/CH6O6P2/c2-8(3,4)1-9(5,6)7/h1H2,(H2,2,3,4)(H2,5,6,7)

InChI key

MBKDYNNUVRNNRF-UHFFFAOYSA-N

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General description

MDP (Methylenediphosphonic acid) is a phosphonic analog of ATP.

Application

Suitable for
  • preparation of analogs of natural di- and tri-phosphates
  • mass spectrometry studies as analytical standard
  • molecular studies related to inflammation

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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J.A. Stock
The Journal of Organic Chemistry, 44, 3997-3997 (1979)
T G Rudd et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 18(9), 872-876 (1977-09-01)
The biologic and imaging characteristics of Tc-99m MDP and Tc-99m PPi were compared in animals and patients using freeze-dried bone-imaging kits. Biodistribution data in rabbits showed Tc-99m MDP had slightly higher bone uptake, significantly lower blood levels, and faster urinary
Phosphonic acid analogs of nucleoside phosphates. I. The synthesis of 5'-adenylyl methylenediphosphonate, a phosphonic acid analog of ATP
Myers TC et al
Journal of the American Chemical Society, 85, 3292-3295 (1963)
R. Engel
Chemical Reviews, 77, 349-349 (1977)
H F Kung et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 19(9), 1027-1031 (1978-09-01)
Bidentate monophosphates--phosphonoacetate (PAA), 2-phosphonoproprionate (PPA), 2-methyl-2-phosphonoproprionate (MPPA), and carbamyl phosphate (CAP)--which are pyrophosphate analogs, were successfully labeled with Sn(II)-reduced [99mTc] pertechnetate in high yield (greater than 95%). Biodistribution studies show that these Tc-99m-labeled monophosphates do localize in bone. At 2
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