Skip to Content
Merck
All Photos(1)

Key Documents

95271

Sigma-Aldrich

Vitamin K1

BioXtra, ≥99.0% (sum of isomers, HPLC), mixture of isomers

Synonym(s):

2-Methyl-3-phytyl-1,4-naphthoquinone, 3-Phytylmenadione, Phylloquinone, Vitamin K1(20)

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C31H46O2
CAS Number:
Molecular Weight:
450.70
Beilstein:
2568816
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.79

biological source

synthetic

Quality Level

product line

BioXtra

Assay

≥99.0% (sum of isomers, HPLC)

form

viscous liquid

impurities

≤20% cis-isomer

ign. residue

≤0.1% (as SO4)

color

light green-yellow to dark green-yellow
light yellow to dark yellow

refractive index

n20/D 1.527 (lit.)

mp

−20 °C (lit.)

density

0.984 g/mL at 25 °C (lit.)

cation traces

Al: ≤5 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤100 mg/kg
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
Na: ≤10 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

storage temp.

2-8°C

SMILES string

O=C(C1=CC=CC=C21)C(C)=C(C/C=C(CCC[C@@H](CCC[C@H](C)CCCC(C)C)C)\C)C2=O

InChI

1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1

InChI key

MBWXNTAXLNYFJB-NKFFZRIASA-N

Looking for similar products? Visit Product Comparison Guide

General description

Vitamin K1, also known as phylloquinone, consists of naphthalenoid and phytyl groups. Phylloquinone is present abundantly in photosynthetic plants and is a major dietary source. It is a fat-soluble vitamin.

Application

<ul>
<li><strong>Nutritional strategies for musculoskeletal health:</strong> Nutritional strategies, including Vitamin K1, optimize musculoskeletal health for fall and fracture prevention beyond traditional nutrients like calcium and vitamin D (Webster et al., 2023 doi:10.1016/j.bonr.2023.101684).</li>
<li><strong>Role in coagulation and bone health:</strong> A comprehensive review highlights Vitamin K1′s role in reducing cardiovascular risks and details its biochemical interactions affecting coagulation and bone health (Zhao et al., 2024 doi:10.1017/jns.2023.106).</li>
</ul>

Biochem/physiol Actions

Vitamin K1 (Phylloquinone) is a lipid soluble polycyclic aromatic ketone used as a cofactor in the formation of coagulation factors II (prothrombin), VII, IX and X; anticoagulant factors protein C and S and as a cell signaling factor.
Vitamin K1 plays a role as a cofactor in the synthesis of γ- carboxy glutamate (Gla), formation of coagulation factors II (prothrombin), VII, IX and X.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Review: Vitamin K and γ-carboxyglutamate biosynthesis; Metabolic functions and mechanism of action

related product

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Waldemar Seel et al.
Scientific reports, 10(1), 330-330 (2020-01-17)
Carotenoids are associated with several important biological functions as antenna pigments in photosynthesis or protectives against oxidative stress. Occasionally they were also discussed as part of the cold adaptation mechanism of bacteria. For two Staphylococcus xylosus strains we demonstrated an
Vitamin K: food composition and dietary intakes
L Booth S
Food & Nutrition Research, 56(1), 5505-5505 (2012)
Metabolism of vitamin K1 (phylloquinone) in man.
Barkhan P and Shearer M J
Proceedings of the Royal Society of Medicine, 70(2), 93-93 (1977)
Vitamin K-containing dietary supplements: comparison of synthetic vitamin K1 and natto-derived menaquinone-7
Schurgers L J, et al.
Blood, 109(8), 3279-3283 (2006)
L Uotila
Scandinavian journal of clinical and laboratory investigation. Supplementum, 201, 109-117 (1990-01-01)
Vitamin K functions in animal cells as the cofactor of the enzyme vitamin K-dependent carboxylase which catalyzes the post-translational formation of gamma-carboxyglutamyl (Gla) residues in specific vitamin K-dependent proteins. These proteins include four blood coagulation factors (prothrombin and Factors VII

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service