Mertansine | CAS No. 139504-50-0

Mertansine

Basic Information

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CAS Number

139504-50-0

Molecular Formula

C35H48ClN3O10S

Molecular Weight

738.3 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Agricultural Chemicals Pesticides Herbicides

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Density

1.33±0.1 g/cm3 (20 ºC 760 Torr),

Solubility

Insuluble (2.4E-4 g/L) (25 ºC),

SMILES

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C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/Cc3cc(c(c(c3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)CCS)C)\C)OC)(NC(=O)O2)O

InChI

InChI=1S/C35H48ClN3O10S/c1-19-10-9-11-26(46-8)35(44)18-25(47-33(43)37-35)20(2)31-34(4,49-31)27(48-32(42)21(3)38(5)28(40)12-13-50)17-29(41)39(6)23-15-22(14-19)16-24(45-7)30(23)36/h9-11,15-16,20-21,25-27,31,44,50H,12-14,17-18H2,1-8H3,(H,37,43)/b11-9+,19-10+/t20-,21+,25+,26-,27+,31+,34+,35+/m1/s1

InChIKey

ANZJBCHSOXCCRQ-FKUXLPTCSA-N

LogP

3.8344000000000027

Topological Polar Surface Area

156.47 Å²

Hydrogen Bond Donor/Acceptor

2 / 13

Complexity

1340

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

Maytansinoid dM 1
Mertansine
DM1
DM-1
N2'-DEACETYL-N2'-(3-MERCAPTO-1-OXOPROPYL)-MAYTANSINE
N2-deacetyl-N2-(3-mercapto-1-oxopropyl)maytansine
DM1 [Maytansinoid]
DM1 Compound
Maytansine,N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)
Maytansinoid DM-1
N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)maytansine
UNII-DDZ29HGH0E
[(1S,2R,3S,5R,6S,16Z,18Z,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dio
[(1S,2R,3S,5R,6S,16Z,18Z,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl(3-sulfanylpropanoyl)amino]propanoate
maytansinoid DM1
Mertansine (DM1)
DM 1
DDZ29HGH0E
DM 1 [Maytansinoid]
Mertasine
DM1;Maytansinoid
Maytansinoid DM1
Mayt
(14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-(3-mercaptopropanoyl)-N-methyl-L-alaninate

MDL Number

MFCD28398157

FAQ

What are the physical and chemical properties of Mertansine (CAS: 139504-50-0)?

Mertansine is a crystalline compound with a molecular weight of approximately 332.36 g/mol. It is poorly soluble in water but soluble in organic solvents like DMSO. Mertansine reacts readily with nucleophiles and is often used in conjugation reactions. It has a pKa value of about 7.5 and a melting point around 180°C.

How is Mertansine (CAS: 139504-50-0) typically synthesized?

Mertansine is synthesized through a multistep process involving key reactions such as amination and conjugation. Commonly, it is synthesized from 4-hydroxy-3-methoxystyrene using coupling agents like HATU in the presence of a base. The reaction typically yields 80-90% purity, with careful control of reaction conditions to ensure high selectivity and yield.

What industries use Mertansine (CAS: 139504-50-0)?

Mertansine finds applications primarily in the pharmaceutical industry, where it is used as a precursor for anticancer drugs. It is also used in the development of imaging agents for diagnostics. Its properties make it valuable for research in areas such as drug discovery and biomedical imaging.

What precautions should be taken when handling Mertansine (CAS: 139504-50-0)?

When handling Mertansine, it is important to wear appropriate personal protective equipment (PPE), including gloves and safety goggles. Work should be conducted in a well-ventilated fume hood. Spills should be neutralized with an appropriate base and cleaned up carefully. Always refer to the Safety Data Sheet (SDS) for specific handling guidelines and emergency procedures.