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D4287

Sigma-Aldrich

γ,γ-Dimethylallyl pyrophosphate triammonium salt

1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3)), ≥90% (TLC)

Synonym(s):

DMAPP

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About This Item

Empirical Formula (Hill Notation):
C5H12O7P2 · 3NH3
CAS Number:
1186-30-7
Molecular Weight:
297.18
MDL number:
MFCD00189839
UNSPSC Code:
12352106
PubChem Substance ID:
24893852
NACRES:
NA.25

Quality Level

200

assay

≥90% (TLC)

form

liquid

packaging

vial of 200 μg

concentration

1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3))

storage temp.

−20°C

SMILES string

N.N.N.C\C(C)=C\COP(O)(=O)OP(O)(O)=O

InChI

1S/C5H12O7P2.3H3N/c1-5(2)3-4-11-14(9,10)12-13(6,7)8;;;/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8);3*1H3

InChI key

VBUNGGIXIOHBHL-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

Intermediate in terpene biosynthesis

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

target_organs

Eyes,Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

69.8 °F - closed cup

flash_point_c

21 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
0000414004
0000414004
0000397162
0000326994
0000302142

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Carla Araya-Cloutier et al.
PloS one, 12(3), e0174665-e0174665 (2017-03-30)
Acceptor substrate specificity of Streptomyces roseochromogenes prenyltransferase SrCloQ was investigated using different non-genuine phenolic compounds. RP-UHPLC-UV-MSn was used for the tentative annotation and quantification of the prenylated products. Flavonoids, isoflavonoids and stilbenoids with different types of substitution were prenylated by
Jinyue Liu et al.
Plant & cell physiology, 59(1), 128-141 (2017-11-16)
Prenylated isoflavonoids have been found in several legume plants, and they possess various biological activities that play important roles in both plant defense and human health. However, it is still unknown whether prenylated isoflavonoids are present in the model legume
Xi Zhang et al.
Journal of chromatography. A, 1558, 115-119 (2018-05-19)
The natural rubber molecule is one of the end products of isoprenoids metabolism in the plant. Dimethylallyl diphosphate (DMAPP) and farnesyl pyrophosphate (FPP) are two typical isoprenoids which control the rate of biosynthesis and the molecular weight of natural rubber.
Keisuke Yoneyama et al.
Plant & cell physiology, 57(12), 2497-2509 (2016-12-18)
Soybean (Glycine max) accumulates several prenylated isoflavonoid phytoalexins, collectively referred to as glyceollins. Glyceollins (I, II, III, IV and V) possess modified pterocarpan skeletons with C
Haibing He et al.
Nature communications, 11(1), 3958-3958 (2020-08-10)
Catalytic versatility is an inherent property of many enzymes. In nature, terpene cyclases comprise the foundation of molecular biodiversity as they generate diverse hydrocarbon scaffolds found in thousands of terpenoid natural products. Here, we report that the catalytic activity of
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