Veratraldehyde

HCID 8419

Basic information

CAS
120-14-9
Standard SMILES
COc1ccc(C=O)cc1OC
InChIKey
WJUFSDZVCOTFON-UHFFFAOYSA-N
Molecular formula
C9H10O3
Average molar mass
166.17 g/mol
Monoisotopic mass
166.06299418

Overview

Veratraldehyde appears as needles or chunky light peach powder. Has an odor of vanilla beans. (NTP, 1992)

Names & identifiers

Preferred name
Veratraldehyde
IUPAC
3,4-dimethoxybenzaldehyde
English name
Veratraldehyde
Molecular formula
C9H10O3
Molecular weight
166.17

Names & synonyms

3,4-DimethoxybenzaldehydeVERATRALDEHYDE120-14-9Veratric aldehydeBenzaldehyde, 3,4-dimethoxy-Vanillin methyl etherVeratrum aldehydeVeratryl aldehydeVeratralp-Veratric aldehyde4-O-Methylvanillin3,4-Dimethoxybenzenecarbonal
Show more names
3,4-DIMETHOXYANILINE204-373-2FEMA 3109METHYL VANILLINMethyl vanilline
Protocatechualdehyde dimethyl etherProtocatechuic aldehyde dimethyl etherFEMA No. 3109DTXSID7026285UI88P68JZDNSC-8500NSC-24521DTXCID406285

Database identifiers

CAS
120-14-9
PubChem CID
8419
DTXSID
DTXSID7026285
ChEMBL
CHEMBL1088937
ChEBI
CHEBI:17098
UNII
UI88P68JZD
EC Number
204-373-2
Nikkaji
J9.907D

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
35.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
12

Experimental & physicochemical properties

FragrancesFragrance Ingredient (Veratraldehyde) -> IFRA transparency List
LogP · 2 items

1.22

1.22

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 4 items

less than 1 mg/mL at 72 °F (NTP, 1992)

6.32 mg/mL at 25 °C

insoluble in cold water; soluble in hot water oils

soluble (in ethanol)

Flash Pointgreater than 230 °F (NTP, 1992)

Physicochemical properties

Melting point
40 · 40-43 °C (lit.)
Boiling point
281 °C · 281 °C (lit.)
Density
1.1708 · 1.1708 (rough estimate)
vapor pressure
0.09 Pa · 0.09Pa at 24℃
refractive index
1.526 · 1.5260 (estimate)
FEMA
3109 · 3109 | VERATRALDEHYDE

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1759 reports by companies from 13 notifications to the ECHA C&L Inventory.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 4 items

Chemical: Benzaldehyde, 3,4-dimethoxy-

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

Status: Active Update: 15-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/20394

3,4-Dimethoxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsThis compound is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Exposure to this compound may cause skin, eye, mucous membrane or upper respiratory tract irritation.
Reactive GroupAldehydes
Reactivity Profile · 1 item

VERATRALDEHYDE is incompatible with strong oxidizing agents and strong bases. (NTP, 1992). VERATRALDEHYDE is an aldehyde. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction).

Air and Water ReactionsInsoluble in water.

Safety & protection

Fire FightingFires involving this compound may be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Protective Action Criteria (PAC) · 3 items

6.0 [mg/m3]

66 [mg/m3]

400 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Safety data

F
9-23
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
YX5088000
hs_code
29124900

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 6 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationBenzaldehyde, 3,4-dimethoxy-: ACTIVE
Applications · 3 items

OccurrenceReported among the constituents of the essential oils of Cymbopogon javanensis and Eryngium poterium. Also reported found in raspberry, ginger, peppermint oil, Bourbon vanilla and mastic gum oil.

UsesVeratraldehyde was used in the preparation of 4-chloromethyl-2-(dimethoxyphenyl)-1,3-dioxolane. It was used in the synthesis of (+)-lithospermic acid, having anti-HIV activity. It forms 1:1 inclusion complexes with cyclodextrins. It reacts with 3-acetyl-2,5-dimethythiophene to yield chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one.

General DescriptionNeedles or chunky light peach powder. Has an odor of vanilla beans.

Preparation methods

PreparationIt can be derived from the reaction of 3-methoxy-4-hydroxybenzaldehyde (vanillin) and dimethyl sulfate, or derived from the methylation of dimethyl sulfate with vanillin in alkaline conditions.

PreparationPrepared from vanillin by methylation of vanillin with dimethylsulfate under mildly alkaline conditions.

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]
南京一化生物科技有限公司13429882898; 13429882898
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Veratraldehyde is a dimethoxybenzene that is benzaldehyde substituted by methoxy groups at positions 3 and 4. It is found in peppermint, ginger, raspberry, and other fruits. It has a role as an antifungal agent. It is a member of benzaldehydes and a dimethoxybenzene.

Related reactions

389 records

Compound notes

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