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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)

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About This Item

Empirical Formula (Hill Notation):
C31H46O2
CAS Number:
84-80-0
Molecular Weight:
450.70
Beilstein:
2568816
EC Number:
201-564-2
MDL number:
MFCD00214063
UNSPSC Code:
12352205
PubChem Substance ID:
57653664
NACRES:
NA.79
Pricing and availability is not currently available.

biological source

synthetic

Quality Level

200

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

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General description

Vitamin K1, also known as phylloquinone, consists of naphthalenoid and phytyl groups.[1] Phylloquinone is present abundantly in photosynthetic plants and is a major dietary source.[2] It is a fat-soluble vitamin.[3]

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.[4]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Review: Vitamin K and γ-carboxyglutamate biosynthesis[5]; Metabolic functions and mechanism of action[6]

related product

Product No.
Description
Pricing

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4029
BCCL8391
BCCK3927
BCCH1231
BCCJ3063

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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
Phylloquinone (vitamin K1): occurrence, biosynthesis and functions
Basset J G, et al.
Mini-Reviews in Medicinal Chemistry, 17(12), 1028-1038 (2017)
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)
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 and gamma-carboxyglutamate biosynthesis.
R E Olson et al.
Vitamins and hormones, 35, 59-108 (1977-01-01)
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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  3. I buy the 250mg bottle and I was wondering about the concentration of the bottle because it arrives as a viscous liquid. It is very important to me to know about the concentration of the liquid to work with it.

    1 answer

    1. Product No. 95271 contains neat Vitamin K1 specified at ≥99.0% purity. Using the minimum specified purity, density, and molecular weight of Vitamin K1, this neat product would have a concentration of about 2.16 M at 25 °C.

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