85-91-6 Usage
Description
Methyl 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.
Chemical Properties
Different sources of media describe the Chemical Properties of 85-91-6 differently. You can refer to the following data:
1. Methyl-n-methylanthranilate has an orange and mandarin peel-like odor and a musty, grape-like flavor; somewhat
more berry-like than grape.
2. Methyl N-Methylanthranilate is the main
component of petitgrain oils from mandarin leaves and is also found in mandarin
oil. It is a pale yellow, fluorescent liquid with a delicate mandarin odor. The ester
can be prepared by methylation ofmethyl anthranilate. It is used in soap and cosmetic
perfumes as well as in aromas, particularly for mandarin flavors.
Occurrence
Reported 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.
Uses
Different sources of media describe the Uses of 85-91-6 differently. You can refer to the following data:
1. It is
used as a flavorant in a wide range of foods (particularly flour
and sugar confections).
2. Methyl 2-(Methylamino)benzoate is one of many volatile components from mango cultivars.
Preparation
By methylation of methyl anthranilate or esterification of N-methylanthranillic acid.
Production Methods
Methyl N-methanthranilate is a component of mandarin and
mandarin tree leaf essential oil. It is also found in oil from
bulbs of Kaempferia ethelae L., hyacinth flowers, and orange
petitgrain . It is synthesized by methylation of methyl
anthranilate or esterification ofN-methylanthranilic acid.
Taste threshold values
Taste characteristics at 10 ppm: fruity grape skin, anthranilate-like with a woody and floral nuance
Synthesis Reference(s)
The Journal of Organic Chemistry, 49, p. 3373, 1984 DOI: 10.1021/jo00192a024
Toxicity evaluation
The acute oral LD50 value in rats was reported as 3.7 ml/kg (Levenstein, 1974). The acute oral LD50 in female rats was reported to be between 2.25 g/kg (no deaths) and 3.38 g/kg (100% deaths) (Gaunt, Sharratt, Grasso & Wright, 1970). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Levenstein, 1974). The LC 50 for larvae of Tribolium destructor was found to be 0-1151 mg/cm3 (Vasechko, Kuznetsov, Smelyanets & Guznenok, 1970).
Safety Profile
Poison by intravenous
route. Moderately toxic by ingestion.
Combustible liquid. When heated to
decomposition it emits toxic fumes of NOx.
See also ESTERS.
Check Digit Verification of cas no
The CAS Registry Mumber 85-91-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 5 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 85-91:
(4*8)+(3*5)+(2*9)+(1*1)=66
66 % 10 = 6
So 85-91-6 is a valid CAS Registry Number.
85-91-6Relevant articles and documents
Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins
Qian, Peng,Liu, Jiaojiao,Zhang, Yan,Wang, Zhiyong
, p. 16008 - 16015 (2021/07/31)
A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.
Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer
Wang, Lei,Fang, Kun,Cheng, Junfei,Li, Yu,Huang, Yahui,Chen, Shuqiang,Dong, Guoqiang,Wu, Shanchao,Sheng, Chunquan
, p. 696 - 713 (2020/02/04)
Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.
Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene
Frost, Grant B.,Mittelstaedt, Michaela N.,Douglas, Christopher J.
, p. 1727 - 1732 (2019/01/09)
Alkenes can be cleaved by means of the (3+2) cycloaddition and subsequent cycloreversion of 1,3-dipoles, classically ozone (O3), but the azide (R?N3) variant is rare. Chemoselectivity for these azide to alkene diazo group transfers (DGT) is typically disfavored, thus limiting their synthetic utility. Herein, this work discloses a palladium-catalyzed intramolecular azide to alkene DGT, which grants chemoselectivity over competing aziridination. The data support a catalytic cycloreversion mechanism distinct from other known metal-catalyzed azide/alkene reactions: nitrenoid/metalloradical and (3+2) cycloadditions. Kinetics experiments reveal an unusual mechanistic profile in which the catalyst is not operative during the rate-controlling step, rather, it is active during the product-determining step. Catalytic DGT was used to synthesize N-heterocyclic quinazolinones, a medicinally relevant structural core. We also report on the competing aziridination and subsequent ring expansion to another N-heterocyclic core structure of interest, benzodiazepinones.
