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Phytomenadione, Phytonadione, фитоменадион ,فيتوميناديون ,

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Vitamin K1.png

ChemSpider 2D Image | Phylloquinone | C31H46O2

Phytomenadione,

PHYTONADIONE, Phylloquinone

Molecular Formula: C31H46O2
Molecular Weight: 450.707 g/mol
[R-[R*,R*-(E)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione
1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl)-
2′,3′-trans-Vitamin K1
фитоменадион [Russian] [INN]
فيتوميناديون [Arabic] [INN]
2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione
 CAS 84-80-0[RN]
Antihemorrhagic vitamin
Aqua mephyton
AQUAMEPHYTON
Combinal K1
Kativ N
Kephton
Kinadion
K-Ject
KONAKION
Mono-kay
Phyllochinonum
Phylloquinone (8CI)
Optical Rotatory Power -0.28 ° Solv: 1,4-dioxane (123-91-1); Wavlen: 589.3 nm; Temp: 25 °CKarrer, P.; Helvetica Chimica Acta 1944, VOL 27, PG317-19

 

MASS

 

1H NMR

400 MHZ CDCL3

 

13C NMR

  1. Murahashi, Shun-ichi; European Journal of Organic Chemistry 2011, VOL2011(27), P5355-5365 
  2. Huang, Zhihong; Advanced Synthesis & Catalysis 2007, VOL349(4+5), PG539-545 

IR LIQ FILM

 

Phylloquinone is a family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.

Phytomenadione, also known as vitamin K1 or phylloquinone, is a vitamin found in food and used as a dietary supplement.[1][2] As a supplement it is used to treat certain bleeding disorders.[2] This includes in warfarin overdosevitamin K deficiency, and obstructive jaundice.[2] It is also recommended to prevent and treat hemorrhagic disease of the newborn.[2] Use is typically recommended by mouth or injection under the skin.[2] Use by injection into a vein or muscle is recommended only when other routes are not possible.[2] When given by injection benefits are seen within two hours.[2]

Common side effects when given by injection include pain at the site of injection and altered taste.[2] Severe allergic reactions may occur with injected into a vein or muscle.[2] It is unclear if use during pregnancy is safe; however, use is likely okay during breastfeeding.[3] It works by supplying a required component for making a number of blood clotting factors.[2] Found sources include green vegetables, vegetable oil, and some fruit.[4]

Phytomenadione was first isolated in 1939.[5] It is on the World Health Organization’s List of Essential Medicines, the most effective and safe medicines needed in a health system.[6] The wholesale cost in the developing world is about 0.11 to 1.27 USD for a 10 mg vial.[7]In the United States a course of treatment costs less than 25 USD.[8] In 1943 Edward Doisy and Henrik Dam were given a Nobel Prizefor its discovery.[5]

Terminology

Phytomenadione is often called phylloquinone or vitamin K,[9] phytomenadione or phytonadione. Sometimes a distinction is made between phylloquinone, which is considered to be a natural substance, and phytonadione, which is considered to be a synthetic substance.[10]

stereoisomer of phylloquinone is called vitamin k1 (note the difference in capitalization).

Chemistry

Vitamin K is a fat-soluble vitamin that is stable in air and moisture but decomposes in sunlight. It is a polycyclic aromatic ketone, based on 2-methyl1,4-naphthoquinone, with a 3-phytyl substituent. It is found naturally in a wide variety of green plants, particularly in leaves, since it functions as an electron acceptor during photosynthesis, forming part of the electron transport chain of photosystem I.

Phylloquinone is an electron acceptor during photosynthesis, forming part of the electron transport chain of Photosystem I.

The best-known function of vitamin K in animals is as a cofactor in the formation of coagulation factors II (prothrombin), VII, IX, and X by the liver. It is also required for the formation of anticoagulant factors protein C and S. It is commonly used to treat warfarin toxicity, and as an antidote for coumatetralyl.

Vitamin K is required for bone protein formation.

SYN

e-EROS Encyclopedia of Reagents for Organic Synthesis, 1-2; 2001

WO2016060670

 

PAPERS

Helvetica Chimica Acta (1944), 27, 317-19.

PATENT

US 2683176

CN 105399615

WO 2016060670

References

  1. Jump up^ Watson, Ronald Ross (2014). Diet and Exercise in Cystic Fibrosis. Academic Press. p. 187. ISBN 9780128005880.
  2. Jump up to:a b c d e f g h i j “Phytonadione”. The American Society of Health-System Pharmacists. Retrieved 8 December 2016.
  3. Jump up^ “Phytonadione Use During Pregnancy”Drugs.com. Retrieved 29 December 2016.
  4. Jump up^ “Office of Dietary Supplements – Vitamin K”ods.od.nih.gov. 11 February 2016. Retrieved 30 December 2016.
  5. Jump up to:a b Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 243. ISBN 9780471899792.
  6. Jump up^ “WHO Model List of Essential Medicines (19th List)” (PDF). World Health Organization. April 2015. Retrieved 8 December 2016.
  7. Jump up^ “Vitamin K1”International Drug Price Indicator Guide. Retrieved 8 December 2016.
  8. Jump up^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 229. ISBN 9781284057560.
  9. Jump up^ Haroon, Y.; Shearer, M. J.; Rahim, S.; Gunn, W. G.; McEnery, G.; Barkhan, P. (June 1982). “The content of phylloquinone (vitamin K1) in human milk, cows’ milk, and infant formula foods determined by high-performance liquid chromatography”J. Nutr112 (6): 1105–1117. PMID 7086539.
  10. Jump up^ “Vitamin K”. Retrieved 2009-03-18.
Phytomenadione
Vitamin K1.png
Clinical data
Trade names Mephyton, others
Synonyms Vitamin K1, phytonadione, phylloquinone
AHFS/Drugs.com Monograph
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
by mouth, subQ, IM, IV
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard 100.001.422
Chemical and physical data
Formula C31H46O2
Molar mass 450.70 g/mol
3D model (JSmol)

/////////////PHYTONADIONE, фитоменадион ,فيتوميناديون PHYTONADIONE, Phylloquinone

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT : Yellow viscous oil (Ref. 0001)


REFRACTIVE INDEX : n20D=1.5263(Ref. 0010)

OPTICAL ROTATION : [a]25D=-28deg(Ref. 0001)Optical rotation
[Table ] (Ref. 0010)

SOLUBILITY : Insol in water. Sparingly sol in methanol; sol in ethanol, acetone, benzene, petr ether, hexane, dioxane, chloroform, ether, other fat solvents and in vegetable oils(Ref. 0001)
SPECTRAL DATA
UV SPECTRA : Uv max (petr ether) 242, 248, 260, 269, 325 nm (E1%1cm396, 419, 383, 387, 68) (Ref. 0001). Uv max (ethanol) 243, 248, 262, 270, 330 nm (Ref. 0002).
(UV Ref. 0010)Em at 248 nm (EtOH) =18,900 (Ref. 0002/0006).

IR SPECTRA : (liquid) : 6.05m (CO), 6.21, 6.28m (aromatic nucleus) (Ref. 0008)
(IR Ref. 0010)
[Table 0002] (Ref. 0010)

NMR SPECTRA : at 60 MHz in CDCl3, i nternal standard Si(CH3)4: multiplet at 453-486 Hz (4 aromatic H), triplet at 302 Hz (J=7 Hz) (olefinic H at C2. , doublet at 201 Hz ) (J=7 Hz) (CH2.-1), singlet at 130 Hz (CH3-2), signal at 107 Hz (trans-methyl group at C3. .(Ref. 0008)
( NMR Ref. 0010) Proton magnetic resonance data

MASS SPECTRA : [Spectrum  (Ref. 0005)
REFERENCES

[0001]

AUTHOR : Anonym. (1989) Vitamin K1 in The Merck Index , 11th edition (Budavari, S., O’Neil, M. J., Smith, A., and Heckelman, P.E., eds), pp1580, Merck & Co., Inc., Rahway, N. J.
TITLE :
JOURNAL :
VOL : PAGE : – ()

[0002]

AUTHOR : Dunphy,P.J., and Brodie,A.F.
TITLE : The structure and function of quinones in respiratory metabolism.
JOURNAL : Methods in Enzymology
VOL : 18 PAGE : 407 -461 (1971)

[0005]

AUTHOR : Di Mari, S. J., Supple, J. H., and Rapoport, H.
TITLE : Mass spectra of naphthoquinones. Vitamin K1(20) PubMed ID:5910960
JOURNAL : J Am Chem Soc.
VOL : 88 PAGE : 1226-1232 (1966)

[0006]

AUTHOR : Suttie,W.J. (1991) Vitamin K, in Handbook of Vitamins (2nd ed., Machlin,L.J., ed) , pp145-194, Marcel Dekker, Inc., New York
TITLE :
JOURNAL :
VOL : PAGE : – ()

[0007]

AUTHOR : Kodaka,K., Ujiie,T.,Ueno,T., and Saito,M.
TITLE : Contents of Vitamin K1 and Chlorophyll in Green Vegetables.
JOURNAL : J Jpn Soc Nutr Food Sci
VOL : 39 PAGE : 124 -126 (1986)

[0008]

AUTHOR : Mayer,H., and Isler,O .
TITLE : Synthesis of Vitamin K.
JOURNAL : Methods in Enzymology
VOL : 18 PAGE : 491 -547 (1971)

[0009]

AUTHOR : Naruta,Y., and Maruyama,K.
TITLE : Regio- and sterocontrolled polyprenylation of quinones. A new synthetic method of vitamin K series.
JOURNAL : Chemistry Lett
VOL : PAGE : 881 -884 (1979)

[0010]

AUTHOR : Sommer,P., and Kofler,M.
TITLE : Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867
JOURNAL : Vitamins and Hormones
VOL : 24 PAGE : 349 -399 (1966)

[0011]

AUTHOR : Bristol, J. A., Ratcliffe, J. V., Roth, D. A., Jacobs, M. A., Furie, B. C., and Furie, B.
TITLE : Biosynthesis of prothrombin: intracellular localization of the vitamin K-dependent carboxylase and the sites of gamma-carboxylation PubMed ID:8839851
JOURNAL : Blood.
VOL : 88 PAGE : 2585-2593 (1996)

[0022]

AUTHOR : Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K.
TITLE : Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953
JOURNAL : J Chromatogr.
VOL : 489 PAGE : 291-301 (1989)

 

//////////////

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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