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Dayang Chem (Hangzhou) Co., Ltd.
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Product Name: Menatetrenone
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Henan Tianfu Chemical Co., Ltd.
China
Product Name: Menatetrenone,863-61-6
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863-61-6

863-61-6 structure

863-61-6 structure

Name: Menatetrenone
Chemical Name: menatetrenone
CAS Number: 863-61-6
Molecular Formula: C₃₁H₄₀O₂
Molecular Weight: 444.648
Catalog: API Vitamins and minerals Vitamin C drugs
Create Date: 2018-06-26 17:38:07
Modify Date: 2026-06-30 18:32:34
Menaquinone-4 is a vitamin K, used as a hemostatic agent, and also a adjunctive therapy for the pain of osteoporosis.

Name	menatetrenone
Synonyms	[R-[R,R-(Z)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione Menatetrenone //BP MENAQUINONE 4 Vitamin K2(20),MK-4 JP14 powder 2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]naphthoquinone 1,4-naphthoquinone,2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen vitamink2(sub20) Phytonadione,(Z) 2-Methyl-3-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)naphthalene-1,4-dione VitaminK2Oil Menaquinone 4 (Mixture of cis-trans isoMers) MK 4 Menatetrenone (MK-4) Menatetrenone(11-8) Phytomenadione,(Z) MENAQUINONE Phylloquinone,cis Glakay 2-Methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione 2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]naphthalene-1,4-dione 2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthalenedione 2-Methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-yl]-1,4-naphthoquinone Vitamin K2(20),MK4 powder vitamin K2 Menatetrenone 1,4-Naphthalenedione, 2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-yl] (E,E,E)-2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthalenedione Vitamin K2 Menatetrenone (Vitamin MK4, E3100) Metetrenone kaytwo Vitamin K2(20),MK4 oil Vitamin K2(MK-4) 2-Methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1,4-naphthoquinone Phylloquinone,(Z) Vitamin K2 (tn) VitaminK2Powder Menaquinone4, Menatetrenone VitaminK2Min.Powder Vitamin K2 (MK-4) solution menaquinon-4 Vitamin K2,MK4,menaquinone, menaquinon-4, menatetrenone, menatetren, menatetrenona, menatetrenonum UNII-A034SE7857 component MBWXNTAXLNYFJB-ODDKJFTJSA-N MENAQUINONE (K2) 100MG NEAT cis-Phylloquinone Vitamin MK-4 2-methyl-3-((E)-3,7,11,15-tetramethyl-hexadec-2-enyl)-[1,4]naphthoquinone VITAMIN K2(MENAQUINONE-4)(SH) 2-methyl-3-trans-tetraprenyl-1,4-naphthoquinone Vitamin K2(20),MK4 mk(sub4) 2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecaenyl]naphthoquinone cis-Vitamin K1 Vitamin K2-Menatetrenone ( MK-4 ) menaquinonek(sub4) e3100 k2(sub20) K220 menatetranone D00100 Menaquinone4, Menatetrenone, VitaminK2 MFCD00079646 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoqu Menatetrenone (jp15/inn) MENATETRENONE Menaquinone-4 Standd 2-Methyl-3-geranylgeranyl-1,4-naphthoquinone Menaquinone K4 menaquinone-4 Menatetrenone RS VitaminK2

Description	Menaquinone-4 is a vitamin K, used as a hemostatic agent, and also a adjunctive therapy for the pain of osteoporosis.
Related Catalog	Signaling Pathways >> Others >> Others Natural Products >> Others Research Areas >> Others
In Vitro	Menaquinone-4 (MK-4, 0, 1, 5, 10 μM) increases the ALP activity in Caco-2 cells. Menaquinone-4 (1 μM) significantly increases intensities of hSI expression[1].
In Vivo	Menaquinone-4 (K2, 0.2 g/kg diet) in HF-K2 group produces epididymal fat in C57BL/6J mice, and also increases the bone density of mice[2].
Cell Assay	Caco-2 cells are plated at a density of 2-5 × 104 cells/cm2 onto a 35-mm dish. Cells are incubated for 2 to 3 days until 60%-70% confluency, and desired concentrations of Menaquinone-4 (0, 1.0, 5.0, and 10.0 μM) are added. The final concentration of the vehicle is 0.1% of the culture medium, and the culture medium is changed twice a week. Cells are assayed on days 0, 3, 7, and 11 after the addition of Menaquinone-4[1].
Animal Admin	Forty-two male, 4-week-old C57BL/6J mice provided with feed and drink ad libitum. For environmental adaptation, the animals had 1 week of circulation, and then are provided with the experimental diet after being randomly divided into 6 groups (7 animals in each group; randomized block design). The AIN-93G diets consist of a normal diet (N), normal diet + vitamin K1 (N-K1), normal diet + vitamin Menaquinone-4 (N-K2), 45% high-fat diet (HF), 45% high-fat diet + vitamin K1 (HF-K1), and a 45% high-fat diet + vitamin Menaquinone-4 (HF-K2). The vitamin K1 and vitamin Menaquinone-4 contents are 200 mg/1,000 g, and the diet is provided in pellet form. Body weight is measured once a week, and the food efficiency ratio (FER) is calculated by dividing the increased body weight from day 1 to the final day by the food intake amount during the experiment period. For fat amount measurement, the epididymal fat, perirenal fat, and retroperitoneal fat are extracted from dead animal subjects, are washed with 0.9% NaCl, dried by filter paper, and then are weighed[2].
References	[1]. Noda S, et al. Menaquinone-4 (vitamin K2) up-regulates expression of human intestinal alkaline phosphatase in Caco-2 cells. Nutr Res. 2016 Nov;36(11):1269-1276. [2]. 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.

Density	1.0±0.1 g/cm3
Boiling Point	570.6±50.0 °C at 760 mmHg
Melting Point	350ºC
Molecular Formula	C₃₁H₄₀O₂
Molecular Weight	444.648
Flash Point	208.3±27.1 °C
Exact Mass	444.302826
PSA	34.14000
LogP	10.94
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.539
Storage condition	−20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL9279500

CHEMICAL NAME :: 1,4-Naphthoquinone, 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecat etraenyl)-

CAS REGISTRY NUMBER :: 863-61-6

LAST UPDATED :: 199606

DATA ITEMS CITED :: 24

MOLECULAR FORMULA :: C31-H40-O2

MOLECULAR WEIGHT :: 444.71

WISWESSER LINE NOTATION :: L66 BV EVJ C2UY1&3UY1&3UY1&3UY1&1 D1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,445,1971

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 gm/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,445,1971

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,445,1971

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >40 mL/kg

TOXIC EFFECTS :: Skin and Appendages - hair

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,2003,1991

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 mg/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,445,1971

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,445,1971

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,445,1971

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >40 mL/kg

TOXIC EFFECTS :: Skin and Appendages - hair

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,2003,1991

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >1 gm/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,445,1971

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >40 mL/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Blood - pigmented or nucleated red blood cells Biochemical - Effect on specific coenzyme - not otherwise specified

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,2003,1991

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: >10 mL/kg

TOXIC EFFECTS :: Blood - changes in cell count (unspecified)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,2003,1991

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 100 mg/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,461,1971

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >100 mg/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,461,1971 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 43680 mg/kg/52W-C

TOXIC EFFECTS :: Endocrine - changes in spleen weight Blood - normocytic anemia Blood - changes in spleen

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 23,2623,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 420 mg/kg/4W-C

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in spleen weight

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,2017,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 182 gm/kg/13W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 23,2609,1995 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 gm/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,469,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1110 mg/kg

SEX/DURATION :: male 90 day(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 15,1143,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 270 mg/kg

SEX/DURATION :: multigenerations

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 15,1143,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 100 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 4 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 15,1143,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,469,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,469,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 gm/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,469,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 5,469,1971

Symbol	GHS02, GHS07
Signal Word	Danger
Hazard Statements	H225-H302 + H312 + H332-H319
Precautionary Statements	P210-P280-P305 + P351 + P338
Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases	22-24/25
RIDADR	UN 1648 3 / PGII
WGK Germany	3
RTECS	QL9279500

Precursor 8
66958-54-1 39776-45-9 24163-93-7 73875-18-0
53772-33-1 132513-59-8 6138-90-5 53254-60-7
DownStream 1
39776-45-9

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