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Vitamin K1 (Phylloquinone) Sale

(Synonyms: 叶绿醌; Phylloquinone; Phytomenadione) 目录号 : GC32446

A cofactor in the formation of blood-clotting proteins

Vitamin K1 (Phylloquinone) Chemical Structure

Cas No.:84-80-0

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10mM (in 1mL DMSO)
¥495.00
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1g
¥630.00
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5g
¥1,980.00
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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Cell experiment:

Caco-2, HT-29, and SW480 cells are treated with increasing concentrations of vitamin K1 (10, 50, 100, and 200 μM) for 24 h, 48 h, and 72 h. MTT is added to each dish and incubated for 2 h at 37°C. At the end of the incubation period, the medium is removed. The plate is read at 570 nM[2].

Animal experiment:

Rats: For inducing full-thickness wound in rats, the excisional wound model is used. Five groups consisting of 8 rats each are used. Vitamin K cream (1% and 2%, w/w) is prepared in eucerin base and applied on the wound once a day until complete healing had occurred. Healing is defined by decreased wound margin (wound contraction), re-epithelialization, tensile strength and hydroxyproline content. Histopathological examination is also done[5]. Mice: Four-week-old C57BL/6J male mice are fed a 10% fat normal diet group or a 45% kcal high-fat diet group, with or without 200 mg/1000 g vitamin K1 (Normal diet + K1, high-fat diet + K1) and 200 mg/1000 g vitamin K2 (Normal diet + K2, high-fat diet + K2) for 12 weeks[4].

References:

[1]. Basset GJ, et al. Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions. Mini Rev Med Chem. 2016 Jun 22.
[2]. Orlando A, et al. Vitamin K1 exerts antiproliferative effects and induces apoptosis in three differently graded human colon cancer cell lines. Biomed Res Int. 2015;2015:296721.
[3]. Ibarrola-Jurado N, et al. Dietary phylloquinone intake and risk of type 2 diabetes in elderly subjects at high risk of cardiovascular disease. Am J Clin Nutr. 2012 Nov;96(5):1113-8.
[4]. Kim M, et al. Vitamin K1 (phylloquinone) and K2 (menaquinone-4) supplementation improves bone formation in a high-fat diet-induced obese mice. J Clin Biochem Nutr. 2013 Sep;53(2):108-13.
[5]. Hemmati AA, et al. Topical vitamin K1 promotes repair of full thickness wound in rat. Indian J Pharmacol. 2014 Jul-Aug;46(4):409-12.

产品描述

Vitamin K1 is a fat-soluble, dietary nutrient that is essential for the synthesis of proteins important for blood-clotting, bone metabolism, and cell growth.1 It is found in the photosynthetic tissues of green, leafy plants, where it acts as an electron acceptor forming part of the electron transport chain of Photosystem I.2 Vitamin K1 also serves as a precursor to vitamin K2 and is reported to exhibit anticancer activity in various cell lines.3,4

1.Plaza, S.M., and Lamson, D.W.Vitamin K2 in bone metabolism and osteoporosisAltern. Med. Rev.10(1)24-35(2005) 2.Santabarbara, S., Heathcote, P., and Evans, M.C.W.Modelling of the electron transfer reactions in Photosystem I by electron tunnelling theory: The phylloquinones bound to the PsaA and the PsaB reaction centre subunits of PS I are almost isoenergetic to the iron-sulfur cluster FXBiochim. Biophys. Acta1708(3)283-310(2005) 3.Beulens, J.W.J., Booth, S.L., van den Heuvel, E.G.H.M., et al.The role of menaquinones (vitamin K2) in human healthBr. J. Nutr.110(8)1357-1368(2013) 4.Lamson, D.W., and Plaza, S.M.The anticancer effects of vitamin KAltern. Med. Rev.8(3)303-318(2003)

Chemical Properties

Cas No. 84-80-0 SDF
别名 叶绿醌; Phylloquinone; Phytomenadione
Canonical SMILES O=C1C(C)=C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C(C2=C1C=CC=C2)=O
分子式 C31H46O2 分子量 450.7
溶解度 Ethanol : ≥ 50 mg/mL (110.94 mM);DMSO : 5.6 mg/mL (12.43 mM) 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.2188 mL 11.0939 mL 22.1877 mL
5 mM 0.4438 mL 2.2188 mL 4.4375 mL
10 mM 0.2219 mL 1.1094 mL 2.2188 mL
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Research Update

Vitamin K: Double Bonds beyond Coagulation Insights into Differences between Vitamin K1 and K2 in Health and Disease

Int J Mol Sci 2019 Feb 19;20(4):896.PMID:30791399DOI:10.3390/ijms20040896.

Vitamin K is an essential bioactive compound required for optimal body function. Vitamin K can be present in various isoforms, distinguishable by two main structures, namely, Phylloquinone (K1) and menaquinones (K2). The difference in structure between K1 and K2 is seen in different absorption rates, tissue distribution, and bioavailability. Although differing in structure, both act as cofactor for the enzyme gamma-glutamylcarboxylase, encompassing both hepatic and extrahepatic activity. Only carboxylated proteins are active and promote a health profile like hemostasis. Furthermore, vitamin K2 in the form of MK-7 has been shown to be a bioactive compound in regulating osteoporosis, atherosclerosis, cancer and inflammatory diseases without risk of negative side effects or overdosing. This review is the first to highlight differences between isoforms Vitamin K1 and K2 by means of source, function, and extrahepatic activity.

Vitamin K2 Needs an RDI Separate from Vitamin K1

Nutrients 2020 Jun 21;12(6):1852.PMID:32575901DOI:10.3390/nu12061852.

Vitamin K and its essential role in coagulation (vitamin K [Koagulation]) have been well established and accepted the world over. Many countries have a Recommended Daily Intake (RDI) for vitamin K based on early research, and its necessary role in the activation of vitamin K-dependent coagulation proteins is known. In the past few decades, the role of vitamin K-dependent proteins in processes beyond coagulation has been discovered. Various isoforms of vitamin K have been identified, and vitamin K2 specifically has been highlighted for its long half-life and extrahepatic activity, whereas the dietary form Vitamin K1 has a shorter half-life. In this review, we highlight the specific activity of vitamin K2 based upon proposed frameworks necessary for a bioactive substance to be recommended for an RDI. Vitamin K2 meets all these criteria and should be considered for a specific dietary recommendation intake.

Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions

Mini Rev Med Chem 2017;17(12):1028-1038.PMID:27337968DOI:10.2174/1389557516666160623082714.

Background: Phylloquinone is a prenylated naphthoquinone that is synthesized exclusively by plants, green algae, and some species of cyanobacteria, where it serves as a vital electron carrier in photosystem I and as an electron acceptor for the formation of protein disulfide bonds. Objective: In humans and other vertebrates, Phylloquinone plays the role of a vitamin (Vitamin K1) that is required for blood coagulation and bone and vascular metabolism. Phylloquinone from green leafy vegetables and vegetable oil represents the major dietary source of vitamin K for humans. Method: In recent years, reverse genetics and biochemical approaches using the model plant Arabidopsis thaliana have shown that Phylloquinone biosynthesis in plants involves paralogous and multifunctional enzymes, a compartmentation of the corresponding pathway in plastids and peroxisomes, and trafficking of some biosynthetic intermediates within plastids themselves. Furthermore, Phylloquinone biosynthetic intermediates create crucial metabolic branch-points with other plastid-synthesized metabolites such as chlorophylls, tocopherols and salicylate. Results & conclusion: This review presents an update on recent studies of the central role of plastids in the biosynthesis of Phylloquinone, in particular on the discovery of novel enzymatic steps that are likely paradigms for Phylloquinone and menaquinone (vitamin K2)-synthesizing organisms alike.

Vitamin K - sources, physiological role, kinetics, deficiency, detection, therapeutic use, and toxicity

Nutr Rev 2022 Mar 10;80(4):677-698.PMID:34472618DOI:10.1093/nutrit/nuab061.

Vitamin K is traditionally connected with blood coagulation, since it is needed for the posttranslational modification of 7 proteins involved in this cascade. However, it is also involved in the maturation of another 11 or 12 proteins that play different roles, encompassing in particular the modulation of the calcification of connective tissues. Since this process is physiologically needed in bones, but is pathological in arteries, a great deal of research has been devoted to finding a possible link between vitamin K and the prevention of osteoporosis and cardiovascular diseases. Unfortunately, the current knowledge does not allow us to make a decisive conclusion about such a link. One possible explanation for this is the diversity of the biological activity of vitamin K, which is not a single compound but a general term covering natural plant and animal forms of vitamin K (K1 and K2) as well as their synthetic congeners (K3 and K4). Vitamin K1 (Phylloquinone) is found in several vegetables. Menaquinones (MK4-MK13, a series of compounds known as vitamin K2) are mostly of a bacterial origin and are introduced into the human diet mainly through fermented cheeses. Current knowledge about the kinetics of different forms of vitamin K, their detection, and their toxicity are discussed in this review.

MK-7 and Its Effects on Bone Quality and Strength

Nutrients 2020 Mar 31;12(4):965.PMID:32244313DOI:10.3390/nu12040965.

Vitamin K acts as a cofactor and is required for post-translational 纬-carboxylation of vitamin K-dependent proteins (VKDP). The current recommended daily intake (RDI) of vitamin K in most countries has been established based on normal coagulation requirements. Vitamin K1 and menaquinone (MK)-4 has been shown to decrease osteocalcin (OC) 纬-carboxylation at RDI levels. Among the several vitamin K homologs, only MK-7 (vitamin K2) can promote 纬-carboxylation of extrahepatic VKDPs, OC, and the matrix Gla protein at a nutritional dose around RDI. MK-7 has higher efficacy due to its higher bioavailability and longer half-life than other vitamin K homologs. As Vitamin K1, MK-4, and MK-7 have distinct bioactivities, their RDIs should be established based on their relative activities. MK-7 increases bone mineral density and promotes bone quality and strength. Collagen production, and thus, bone quality may be affected by MK-7 or MK-4 converted from MK-7. In this review, we comprehensively discuss the various properties of MK-7.