4-Amino-2-methyl-1-naphthol

Names

[ CAS No. ]:
83-70-5

[ Name ]:
4-Amino-2-methyl-1-naphthol

[Synonym ]:
4-Amino-2-methyl-1-naphthol
4-Amino-2-methyl-1-naphthol hci
synkaminbase
4-amino-2-methylnaphthalen-1-ol
4-amino-2-methyl-1-naphthaleno
kayvisyn
4-Amino-1-hydroxy-2-methyl-naphthalin
1-Naphthalenol, 4-amino-2-methyl-
2-methyl-4-amino-1-naphthol
synkamin
4-amino-2-methyl-1-naphtho
4-amino-2-methyl-1-naphthalenol

Biological Activity

[Description]:

Vitamin K5 (Synkamin) is a photosensitizer and a antimicrobial agent. Vitamin K5 is a specific PKM2 inhibitor with IC50 values of 28, 191 and 120 μM for PKM2, PKM1 and PKL. Vitamin K5 induces apoptosis of colon 26 cells. Vitamin K5 can be used for the research of infection and cancer, and it also can be used as a preservative for pharmaceuticals, foods, and beverages[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

IC50: 28 μM (PKM2), 191 μM PKM1, 120 μM (PKL)[2]

[In Vitro]

Vitamin K5 (0-1600 μmoL/L) 增强 UVA 辐照对大肠杆菌，蜡样芽孢杆菌，铜绿假单胞菌，金黄色葡萄球菌，表皮葡萄球菌和肺炎克雷伯菌的抑菌作用[1]。 Vitamin K5 (250-1000 μmoL/L) 产生超氧阴离子自由基和羟基自由基，在 UVA 2.9 J cm-2 的固定剂量下[1]。 Vitamin K5 (0-100 μM; 1 h) 剂量依赖性地抑制细胞葡萄糖消耗和乳酸生成[2]。 Vitamin K5 剂量依赖性地抑制 colon 26 细胞的增殖[3]。 Vitamin K5 诱导细胞凋亡，增加 colon 26 细胞 caspase-3 活性[3]。

[References]

[1]. Xu F, et al. Vitamin K5 is an efficient photosensitizer for ultraviolet A light inactivation of bacteria. FEMS Microbiol Lett. 2018 Feb 1;365(4).

[2]. Chen J, et al. Vitamin K(3) and K(5) are inhibitors of tumor pyruvate kinase M2. Cancer Lett. 2012 Mar 28;316(2):204-10.

[3]. Ogawa M, et al. Vitamins K2, K3 and K5 exert antitumor effects on established colorectal cancer in mice by inducing apoptotic death of tumor cells. Int J Oncol. 2007 Aug;31(2):323-31.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
385.1±30.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₁H₁₁NO

[ Molecular Weight ]:
173.211

[ Flash Point ]:
186.7±24.6 °C

[ Exact Mass ]:
173.084061

[ PSA ]:
46.25000

[ LogP ]:
1.40

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.712

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL3350000

CHEMICAL NAME :: 1-Naphthol, 4-amino-2-methyl-

CAS REGISTRY NUMBER :: 83-70-5

BEILSTEIN REFERENCE NO. :: 2719282

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H11-N-O

MOLECULAR WEIGHT :: 173.23

WISWESSER LINE NOTATION :: L66J BQ C1 EZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/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

Safety Information

[ HS Code ]:
2922299090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2922299090

[ Summary ]:
2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%