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Merck
CN

D4287

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:
Molecular Weight:
297.18
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25
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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

Biochem/physiol Actions

Intermediate in terpene biosynthesis

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

69.8 °F - closed cup

Flash Point(C)

21 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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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
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
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.
Khiem Nguyen et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 31(11), 4697-4706 (2017-07-15)
Small isoprenoid diphosphates, such as (

Articles

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

胆固醇的生物合成通常发生在肝细胞的内质网中,并以乙酰辅酶A开始,乙酰辅酶A主要来源于线粒体中的氧化反应。乙酰辅酶A和乙酰乙酰辅酶A由HMG-辅酶A合成酶转化为3-羟基-3-甲基戊二酰辅酶A(HMG-辅酶A)。

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