Vitamin K1

Names

[ CAS No. ]:
84-80-0

[ Name ]:
Vitamin K1

[Synonym ]:
KONAKION
Rac-Phytonadione-D7
Phylloquinone-d3
VITAMIN K1 (PHYTONADIONE)
Veda K1
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-1,4-naphthoquinone
Kephton
Antihemorrhagic vitamin
1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl)-
2-METHYL-3-PHYTYL-1,4-NAPHTHOQUINONE
2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione
2',3'-trans-Vitamin K1
AQUAMEPHYTON
Combinal K1
Orakay
1,4-NAPHTHALENEDIONE,2-METHYL-3-[(2E,7R,11R)-3,7,11,15-TETRAMETHYL-2-HEXADECEN-1-YL]-
2-méthyl-3-[(2E,7R,11R)-3,7,11,15-tétraméthylhexadéc-2-én-1-yl]naphtalène-1,4-dione
EINECS 201-564-2
Vitamin K1
Veta K1
[R-[R*,R*-(E)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione
VITAMIN K1-[2H7] (PHYTONADIONE)
Phyllochinonum
Phytonadione, K1
1,4-naphthalenedione, 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-
VITAMIN K/PHYLLOQUINONE
phytomenadione
Kaywan
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalen-1,4-dion
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-naphthoquinone
1,4-Naphthalenedione, 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-
2-Methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione
Aqua mephyton
vitamin K1 quinone
Vitamin K1 (VAN)
Kativ N
K-Ject
VITAMIN K<SUBSCRIPT>1</SUBSCRIPT>
Synthex P
2',3'-t
Phytylmenadione
kativn
Mono-kay
MFCD00214063
PHYTONADIONE
Kinadion
Vitamin- K1
Phylloquinone (8CI)
PHYTOMENADIONE, BP STANDARD

Biological Activity

[Description]:

Vitamin K1 a fat-soluble, naturally occurring vitamin required for blood coagulation and bone and vascular metabolism.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cardiovascular Disease

Natural Products >> Quinones

[In Vitro]

Phylloquinone (Vitamin K1) 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. 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[1]. Vitamin K1 treatment causes a significant antiproliferative effect and induces apoptosis in Caco-2, HT-29, and SW480 cell lines, with the involvement of the MAPK pathway. A concomitant and significant decrease in the polyamine biosynthesis occurr[2].

[In Vivo]

Subjects who increase their dietary intake of vitamin K during the follow-up had a 51% reduced risk of incident diabetes compared with subjects who decrease or does not change the amount of phylloquinone intake[3]. Vitamin K supplementation reverses the high fat diet induced bone deterioration by modulating osteoblast and osteoclast activities and prevent bone loss in a high-fat diet-induced obese mice[4]. Application of vitamin K1 to the skin has been used for suppression of pigmentation and resolution of bruising. The effects produced by the topical vitamin K1 shows significant healing when compared with control group in parameters such as wound contraction, epithelialization period, hydroxyproline content and tensile strength[5].

[Cell Assay]

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 admin]

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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
546.4±50.0 °C at 760 mmHg

[ Melting Point ]:
−20 °C(lit.)

[ Molecular Formula ]:
C₃₁H₄₆O₂

[ Molecular Weight ]:
450.696

[ Flash Point ]:
200.4±27.1 °C

[ Exact Mass ]:
450.349792

[ PSA ]:
34.14000

[ LogP ]:
12.25

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.511

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QJ5800000

CHEMICAL NAME :: 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-

CAS REGISTRY NUMBER :: 84-80-0

LAST UPDATED :: 199701

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C31-H46-O2

MOLECULAR WEIGHT :: 450.77

WISWESSER LINE NOTATION :: L66 BV EVJ C1 D2UY1&3Y1&3Y1&3Y1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 11429 ug/kg/8D-I

TOXIC EFFECTS :: Blood - eosinophilia Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: ARDEAC Archives of Dermatology. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.82- 1960- Volume(issue)/page/year: 121,1421,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >33487 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GWXXBX German Offenlegungsschrift Patent Document. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #2808572

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 17,1339,1967

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 8,25,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >6570 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,653,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4073 No. of Facilities: 394 (estimated) No. of Industries: 4 No. of Occupations: 23 No. of Employees: 26120 (estimated) No. of Female Employees: 15615 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
QJ5800000

[ HS Code ]:
2936290090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2936290090

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