Methyl N-methylanthranilate (HCID 6826)

Names & identifiers

Preferred name: Methyl N-methylanthranilate
IUPAC: methyl 2-(methylamino)benzoate
English name: Methyl 2-(methylamino)benzoate
Molecular formula: C9H11NO2
Molecular weight: 165.19

Names & synonyms

Methyl 2-(methylamino)benzoate85-91-6METHYL N-METHYLANTHRANILATEDimethyl anthranilateMethyl methylaminobenzoateMethyl methanthranilateMethyl methylanthranilateBenzoic acid, 2-(methylamino)-, methyl esterMethyl N-methyl anthranilateN-Methylanthranilic acid, methyl ester2-Methylaminomethyl benzoateMethyl-N-methylanthranilate

Show more names

FEMA 2718DIMETHYLANTHRANILATDimethylanthanilate3-Amino-2-butenamide

Anthranilic acid, N-methyl-, methyl esterFEMA No. 2718Methyl 2-methylaminobenzoateNSC-94065Z37T562P9DTXSID1052581CHEBI:142267RefChem:34802

Database identifiers

CAS: 85-91-6
PubChem CID: 6826
DTXSID: DTXSID1052581
ChEMBL: CHEMBL1409791
ChEBI: CHEBI:142267
UNII: 5Z37T562P9
EC Number: 201-642-6
Nikkaji: J2.411B

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 38.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 12
Formal charge: 0
Complexity: 159

Physicochemical properties

Melting point: 17 · 17-19 °C(lit.)
Boiling point: 256 °C · 256 °C(lit.)
Density: 1.126 g/mL · 1.126 g/mL at 25 °C(lit.)
vapor pressure: 2.74 Pa · 2.74Pa at 25℃
FEMA: 2718 · 2718 | METHYL N-METHYLANTHRANILATE
refractive index: 20 · n20/D 1.579(lit.)
FLAVIS Number: 9.781 · 09.781 | Methyl N-methylanthranilate
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
solubility: 96 %, · Miscible in all proportions with ethanol 96%, DMSO and diethyl ether.
pka: 2.8 · 2.80±0.10(Predicted)
form: 19 °C · 19°C Liquid
color: Colourless to Yellow
PH: 7 · 7-8 (H2O, 20℃)
Odor: 100 % · at 100.00 %. fruity musty sweet neroli powdery phenolic wine
Odor Type: floral
biological source: synthetic
Water Solubility: 329.792 mg/L · 329.792mg/L at 30℃
JECFA Number: 1545 · 1545
BRN: 607217 · 607217
Cosmetics Ingredients Functions: FRAGRANCE
InChI: 1S/C9H11NO2/c1-10-8-6-4-3-5-7(8)9(11)12-2/h3-6,10H,1-2H3
InChIKey: GVOWHGSUZUUUDR-UHFFFAOYSA-N
SMILES: CNc1ccccc1C(=O)OC
LogP: 2.81 · 2.81-3.08 at 25℃
CAS DataBase Reference: 85 · 85-91-6(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): METHYL N-METHYLANTHRANILATE
EWG's Food Scores: 1 · 1-3
FDA UNII: 5 Z37T562P9 · 5Z37T562P9
NIST Chemistry Reference: Benzoic acid,o-(methylamino)-, methyl ester(85-91-6)
EPA Substance Registry System: Methyl N-methyl anthranilate (85-91-6)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 319 · H319
Precautionary statements: 264 · P264-P280-P305+P351+P338-P337+P313
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-36/37/39-22
WGK Germany: 1 · 1
RTECS: 3500000 · CB3500000
TSCA: TSCA listed
HS Code: 2922498590 · 2922498590
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 · Eye Irrit. 2
Hazardous Substances Data: 85 · 85-91-6(Hazardous Substances Data)
REACH Registrations: Active

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 1
tsca: TSCA listed
rtecs: CB3500000
hs_code: 2922498590
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-36/37/39-22
Storage Class: 10 - Combustible liquids
Hazard statements: H319
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2
Precautionary statements: P264-P280-P305+P351+P338-P337+P313
Hazardous Substances Data: 85-91-6(Hazardous Substances Data)

Chemistry & industry

Applications · 4 items

DescriptionMethyl n-methylanthranilate has an orange and mandarin peel-like odor with a musty, grape-like flavor. It is somewhat more berry-like than grape. May be prepared by methylation of methyl anthranilate or esterification of N-methylanthranilic acid.

OccurrenceReported found in mandarin essential oil and mandarin leaves essential oil (50 to 76.5%); also reported in the oil from bulbs of Kaempferia ethelae L., in orange petitgrain, and in the oil from hyacinth flowers. Also reported found in starfruit, orange peel oil and grapefruit juice.

UsesIt is used as a flavorant in a wide range of foods (particularly flour and sugar confections).

UsesMethyl 2-(Methylamino)benzoate is one of many volatile components from mango cultivars.

Preparation methods

PreparationBy methylation of methyl anthranilate or esterification of N-methylanthranillic acid.

Upstream & downstream products

Upstream raw materials

Downstream products

methyl sulfamate Methyl 2-(2-Chloro-N-methylacetamido)benzoate 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

上海泰矶林实业有限公司02150630626 17717886015 · [email protected]

Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Methyl N-methylanthranilate is a methyl ester resulting from the formal condensation of the carboxy group of N-methylanthranilic acid with methanol. It has a role as a fungal metabolite, a plant metabolite and an animal metabolite. It is a benzoate ester, a methyl ester, a secondary amino compound and a substituted aniline. It is functionally related to a N-methylanthranilic acid.