Menadione

Modify Date: 2026-06-29 22:25:26

Menadione Structure
Menadione structure
Common Name Menadione
CAS Number 58-27-5 Molecular Weight 172.18000
Density 1.225 g/cm3 Boiling Point 304.5ºC at 760 mmHg
Molecular Formula C11H8O2 Melting Point 105-107 °C(lit.)
MSDS Chinese USA Flash Point 113.8ºC
Symbol GHS07
GHS07
Signal Word Warning

 Use of Menadione


Menadione, a synthetic naphthoquinone, can be converted to active vitamin K2 in vivo.Target: OthersMenadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent [1].

 Names

This table lists Chinese names, IUPAC names and various aliases of this chemical substance.

Name Menadione
Synonym More Synonyms

 Menadione Biological Activity

This table contains bioactivity, target information and biological‑assay experimental data of this compound.

Description Menadione, a synthetic naphthoquinone, can be converted to active vitamin K2 in vivo.Target: OthersMenadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent [1].
Related Catalog
Target

Human Endogenous Metabolite

References

[1]. http://en.wikipedia.org/wiki/Menadione

 Chemical & Physical Properties

This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.

Density 1.225 g/cm3
Boiling Point 304.5ºC at 760 mmHg
Melting Point 105-107 °C(lit.)
Molecular Formula C11H8O2
Molecular Weight 172.18000
Flash Point 113.8ºC
Exact Mass 172.05200
PSA 34.14000
LogP 2.01190
InChIKey MJVAVZPDRWSRRC-UHFFFAOYSA-N
SMILES CC1=CC(=O)c2ccccc2C1=O
Storage condition Store at RT.
Stability Stable. May be light sensitive. Incompatible with strong oxidizing agents.
Water Solubility INSOLUBLE

 MSDS

This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.

 Toxicological Information

This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QL9100000
CHEMICAL NAME :
1,4-Naphthoquinone, 2-methyl-
CAS REGISTRY NUMBER :
58-27-5
LAST UPDATED :
199710
DATA ITEMS CITED :
30
MOLECULAR FORMULA :
C11-H8-O2
MOLECULAR WEIGHT :
172.19
WISWESSER LINE NOTATION :
L66 BV EVJ C1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
75 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
138 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
230 mg/kg
TOXIC EFFECTS :
Vascular - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10500 mg/kg/30D-I
TOXIC EFFECTS :
Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
775 mg/kg/6D-I
TOXIC EFFECTS :
Blood - pigmented or nucleated red blood cells Blood - changes in spleen Nutritional and Gross Metabolic - changes in iron
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1860 mg/kg/27W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors Tumorigenic - tumors at site of application
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
8400 mg/kg/21W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3 gm/kg
SEX/DURATION :
female 1-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
20 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
Specific locus test

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
10 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 178,57,1987 *** REVIEWS *** TOXICOLOGY REVIEW JOPDAB Journal of Pediatrics. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) V.1- 1932- Volume(issue)/page/year: 59,1,1961 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84779 No. of Facilities: 63 (estimated) No. of Industries: 2 No. of Occupations: 6 No. of Employees: 1170 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84779 No. of Facilities: 771 (estimated) No. of Industries: 5 No. of Occupations: 16 No. of Employees: 6103 (estimated) No. of Female Employees: 2166 (estimated)

 Safety Information

This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R36/37/38;R43
Safety Phrases S26-S36-S37/39-S24
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS QL9100000
HS Code 2914700090

 Synthetic Route

This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.

 Customs

This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.

HS Code 2914690090
Summary 2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

 Articles200

More Articles

This table lists relevant public references with title, journal and publication metadata for this compound.

Hypoxanthine uptake by skeletal muscle microvascular endothelial cells from equilibrative nucleoside transporter 1 (ENT1)-null mice: effect of oxidative stress.

Microvasc. Res. 98 , 16-22, (2015)

Adenosine is an endogenous regulator of vascular tone. This activity of adenosine is terminated by its uptake and metabolism by microvascular endothelial cells (MVEC). The predominant transporter invo...

Minimal detection of nuclear mutations in XP-V and normal cells treated with oxidative stress inducing agents.

J. Biochem. Mol. Toxicol. 28(12) , 568-77, (2014)

Elevated levels of reactive oxygen species (ROS) can be induced by exposure to various chemicals and radiation. One type of damage in DNA produced by ROS is modification of guanine to 7,8-dihydro-8-ox...

Time series analysis of oxidative stress response patterns in HepG2: a toxicogenomics approach.

Toxicology 306 , 24-34, (2013)

Oxidative stress plays an important role in chemically induced liver injury, however, our insight into molecular responses to different oxygen radicals is fragmentary. Since these cellular responses w...

 Synonyms

This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.

Aquakay
Karcon
Kipca
Menadione
Synkay
Koaxin
Kaykot
Kanone
2-methyl-1,4-naphthalenedione
EINECS 200-372-6
Kareon
2-methyl-naphthoquinone
Juva-K
2-methyl-1,4-naphthodione
MFCD00001681
VK3

 Menadione | FAQ

This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.

Q: What is the LogP of Menadione?
A: LogP of Menadione is 2.01190.
Q: What is the molecular weight of Menadione?
A: Molecular weight of Menadione is 172.18000.
Q: What is the CAS number of Menadione?
A: CAS number of Menadione is 58-27-5.
Q: What is the polar surface area (PSA) of Menadione?
A: Polar surface area (PSA) of Menadione is 34.14000.
Q: What are the downstream products of Menadione?
A: Related downstream products(CAS) of Menadione: 111052-03-0;481-85-6;85485-07-0;85485-08-1;85485-05-8;85485-06-9;58-27-5;1059-86-5;2211-27-0;18690-80-7.
Q: What is the English name of Menadione?
A: The English name of Menadione is Menadione.
Q: What is the boiling point of Menadione?
A: Boiling point of Menadione is 304.5ºC at 760 mmHg.
Q: What are the storage conditions for Menadione?
A: Storage conditions for Menadione: Store at RT.
Q: What is the molecular formula of Menadione?
A: Molecular formula of Menadione is C11H8O2.
Q: What are the uses of Menadione?
A: Main uses of Menadione: Menadione, a synthetic naphthoquinone, can be converted to active vitamin K2 in vivo.Target: OthersMenadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent [1].

 Menadionefactory

This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.

Shanghai Nianxing Industrial Co., Ltd
Henan Tianfu Chemical Co., Ltd.
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