| Identification | More | [Name]
Veratraldehyde | [CAS]
120-14-9 | [Synonyms]
3,4-DIMETHOXYBENZALDEHYDE
3,4-DIMETHOXYBENZENECARBONAL
AKOS BBS-00003208
FEMA 3109
LABOTEST-BB LT00235863
METHYL VANILLIN
protocatechualdehyde dimethyl ether
PROTOCATECHUIC ALDEHYDE DIMETHYL ETHER
VANILLIN METHYL ETHER
VERATRALDEHYDE
VERATRIC ALDEHYDE
VERATRUMALDEHYDE
VERATRYL ALDEHYDE
3,4-dimethoxybenzaldehhyde
3,4-dimethoxy-benzaldehyd
4-O-Methylvanillin
Benzaldehyde, 3,4-dimethoxy-veratraldehyde
Protocatechuecaldehyde dimethyl ether
protocatechuecaldehydedimethylether
p-Veratric aldehyde | [EINECS(EC#)]
204-373-2 | [Molecular Formula]
C9H10O3 | [MDL Number]
MFCD00003363 | [Molecular Weight]
166.17 | [MOL File]
120-14-9.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white crystalline solid | [Melting point ]
40-43 °C (lit.) | [Boiling point ]
281 °C (lit.) | [density ]
1.1708 (rough estimate) | [vapor pressure ]
0.09Pa at 24℃ | [FEMA ]
3109 | [refractive index ]
1.5260 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
alcohol: freely soluble | [form ]
Lumps or Fused Solid | [color ]
White to yellow | [Odor]
at 10.00 % in dipropylene glycol. sweet woody vanilla | [Stability:]
Stable. Incompatible with strong bases, strong oxidizing agents. | [Odor Type]
creamy | [Water Solubility ]
<0.1 g/100 mL at 22 ºC | [Sensitive ]
Air Sensitive | [JECFA Number]
877 | [Merck ]
14,9951 | [BRN ]
473899 | [LogP]
0.8 at 25℃ | [CAS DataBase Reference]
120-14-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzaldehyde, 3,4-dimethoxy-(120-14-9) | [EPA Substance Registry System]
120-14-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin.
R36/37/38:Irritating to eyes, respiratory system and skin .
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
YX5088000
| [F ]
9-23 | [TSCA ]
Yes | [HS Code ]
29124900 | [Toxicity]
LD50 orally in Rabbit: 2000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Dimethyl sulfate-->Vanillin | [Preparation Products]
3,4-Dihydroxyphenylacetic acid-->(3,4-Dimethoxyphenyl)acetic acid-->3,4-Dimethoxybenzyl alcohol-->3-PHENYLUMBELLIFERONE-->Methyldopa-->Diaveridine-->7-Hydroxy-6-methoxy-3,4-dihydroisoquinoline-->Fenoldopam-->3,4-Dimethoxyphenylacetone-->B-(3,4-DIMETHOXYPHENYL)-A-CYANOPROPIONALDEHYDE DIMETHYLACETAL-->6,7-Dimethoxy-2,4-Quinazolinedione-->SINENSETIN-->2,6-Bis-(3,4-Dimethoxyphenylmethylene)-Cyclohexanone |
| Hazard Information | Back Directory | [General Description]
Needles or chunky light peach powder. Has an odor of vanilla beans. | [Reactivity Profile]
VERATRALDEHYDE(120-14-9) is incompatible with strong oxidizing agents and strong bases. . VERATRALDEHYDE(120-14-9) 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 & Water Reactions]
Insoluble in water. | [Fire Hazard]
This compound is probably combustible. | [Occurrence]
Reported 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. | [Uses]
Veratraldehyde 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. | [Definition]
ChEBI: 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. | [Aroma threshold values]
Aroma characteristics at 1.0%: phenolic, sweet vanilla, powdery, slightly woody with a candy and cocoa
creaminess. | [Taste threshold values]
Taste characteristics at 50 ppm: phenolic, vanilla, sweet powdery cocoa, creamy, cherry-like with phenolic
and balsamic nuances.. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 69, p. 2070, 1947 DOI: 10.1021/ja01200a517
Organic Syntheses, Coll. Vol. 2, p. 619, 1943
Tetrahedron Letters, 20, p. 975, 1979 | [Flammability and Explosibility]
Notclassified | [Biochem/physiol Actions]
Taste at 50 ppm | [Purification Methods]
Crystallise the ether from diethyl ether, pet ether, CCl4 or toluene. [Beilstein 8 IV 1765.] |
| Questions And Answer | Back Directory | [Chemical properties]
White to brown or blue-gray needle crystal (crystallization in ether); sweet woody fragrance, fragrant grass aroma and strong flavor of vanilla blue; oxidized into odorless 3,4-dimethoxybenzoic acid (veratric acid) in the air; Melting point 43~45℃; Insoluble in cold water; soluble in hot water, ethanol and oil.
Natural products exist in the Java citronella oil and Hu Xanthium parsley oil and so on.
Use GB 2760 a 1996 provisions for the use of food spices. | [Application]
- This product is the intermediate of organic synthesis. In pharmaceutical industry, it is used to synthesize methamphetamine and also used in the production of veterinary drug sulfonamide synergist. Adding 0.02% (weight) of this veterinary drug into feed can increase the efficiency of the iodine drug synergistic added in feed, which can prevent and control the poultry bacterial infection.
- Used as pharmaceutical intermediate and mainly used for antibiotic drug synthesis.
| [Preparation]
It 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. |
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