5-Methylfurfural

HCID 12097

Basic information

CAS
620-02-0
Standard SMILES
Cc1ccc(C=O)o1
InChIKey
OUDFNZMQXZILJD-UHFFFAOYSA-N
Molecular formula
C6H6O2
Average molar mass
110.11 g/mol
Monoisotopic mass
110.03677943

Overview

5-methyl-2-furaldehyde is a member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and methyl groups, respectively. It has a role as an EC 2.2.1.6 (acetolactate synthase) inhibitor, a flavouring agent, a Maillard reaction product and a human metabolite. It is an aldehyde and a member of furans.

Names & identifiers

Preferred name
5-Methylfurfural
IUPAC
5-methylfuran-2-carbaldehyde
English name
5-Methyl furfural
Molecular formula
C6H6O2
Molecular weight
110.11

Names & synonyms

5-METHYLFURFURAL5-Methylfuran-2-carbaldehyde5-Methyl-2-furaldehyde5-Methyl-2-furfural5-Methyl-2-furancarboxaldehyde2-Furancarboxaldehyde, 5-methyl-5-methyl-2-furancarbaldehydeEINECS 210-622-6Furfural, 5-methyl-CCRIS 2921BRN 01068955-Methyl-2-furanaldehyde
Show more names
FEMA 2702Methylfurfural5-methyl fural
5-MethyIfurfuralUNII-4482BZC72D5-METHYLFURAN-2-ALDEHYDEAI3-365915-17-09-00404 (Beilstein Handbook Reference)METHYL-5-FURALDEHYDEMETHYL FURFURAL, 5-DTXSID1060714

Database identifiers

CAS
620-02-0
PubChem CID
12097
DTXSID
DTXSID1060714
ChEMBL
CHEMBL2230304
ChEBI
CHEBI:2091
UNII
4482BZC72D
EC Number
210-622-6
Nikkaji
J37.047I

Properties

Computed structural properties

XLogP
0.7
Topological polar surface area
30.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
8

Experimental & physicochemical properties

SpringerMaterials PropertiesSchoenflies notation
FragrancesFragrance Ingredient (5-Methylfurfural) -> IFRA transparency List
LogP · 2 items

0.67

0.67

Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.098-1.108
Flavoring AgentsEU Flavoring substances

Physicochemical properties

Melting point
171 °C · 171 °C
Boiling point
187 · 187-189 °C(lit.)
Density
1.107 g/mL · 1.107 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.531
FEMA
2702 · 2702 | 5-METHYLFURFURAL
FLAVIS Number
13.001 · 13.001 | 5-Methylfurfural

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 88.4% (380 of 430) of all reports.

Warning

H315 (11.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 430 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: 2-Furancarboxaldehyde, 5-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Furancarboxaldehyde, 5-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (11.4%)

Safety data

wgk
2
tsca
TSCA listed
rtecs
LT7032500
hs_code
29329995
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information2-Furancarboxaldehyde, 5-methyl-: ACTIVE
Applications · 4 items

OccurrenceReported found in sour cherry, apple, orange juice, cranberry, blueberry, guava, grapes, raisin, peach, blackberry, strawberry jam, asparagus, carrot, onion, potato, bell pepper, tomato, cinnamon, bark, clove bud, bread, parmesan cheese, yogurt, butter, egg, fatty fish, beef, pork liver, beer, cognac, coffee, tea, barley, filberts, popcorn, peanuts, oats, soybean, roasted coconut, cloudberry, passion fruit, pecan, mushroom, starfruit, trassi, sesame seed, mango, tamarind, rice bran, quince, sweet potato, sukiyaki, calamus, licorice, malt, wort, elderberry, mangosteen, kiwifruit, buchu oil, Bourbon vanilla, wild rice, chicory root, shrimp, oyster, clam, okra, pistachio nut and maté

Uses5-Methyl-2-furaldehyde is used as a perfuming agent. It is used a smoke with essence.

Uses5-methylfurfural is an intermediate for the synthesis of s-bioallethrin and prallethrin.It used for blending coffee, chocolate, nuts, caramel, spices and on food fragrance. Used in the synthesis of pharmaceutical intermediates.

General Description5-Methylfurfural is formed during the photoexposition of ranitidine hydrochloride. It is employed as potential age marker for Madeira wine. It is a volatile compound present in Lavandula stoechas, Lavandula angustifolia and Lavandula angustifolia x latifolia unifloral honeys.

Preparation methods

PreparationFrom sucrose with HCl, followed by treating with stannous chloride; 5-Methyl furfural is produced by distillation of various methylpentoses with acid together.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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]
枣庄九星生物科技有限公司0632-3759569 13589608009
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: 5-methyl-2-furaldehyde is a member of furans and an aldehyde. It has a role as a Maillard reaction product, a human metabolite, an EC 2.2.1.6 (acetolactate synthase) inhibitor and a flavouring agent.

Related reactions

82 records

Compound notes

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