Basic information
- Standard SMILES
COc1cc(C=O)cc(OC)c1O- InChIKey
KCDXJAYRVLXPFO-UHFFFAOYSA-N- Molecular formula
- C9H10O4
- Average molar mass
- 182.17 g/mol
- Monoisotopic mass
- 182.0579088
Names & identifiers
- Preferred name
- Syringaldehyde
- IUPAC
- 4-hydroxy-3,5-dimethoxybenzaldehyde
- English name
- Syringaldehyde
- Molecular formula
- C9H10O4
- Molecular weight
- 182.17
Names & synonyms
SYRINGALDEHYDE134-96-34-Hydroxy-3,5-dimethoxybenzaldehyde3,5-Dimethoxy-4-hydroxybenzaldehydeSyringic aldehydeSyringylaldehydeBenzaldehyde, 4-hydroxy-3,5-dimethoxy-SyringealdehydeGallaldehyde 3,5-dimethyl ether2ZR01KTT21NSC-411532,6-DIMETHOXY-4-FORMYLPHENOL
Show more names
Lilac aldehydeFEMA 4049SYRINGA ALDEHYDESyringSyringaL
DTXSID2059643FEMA NO. 4049CHEBI:67380SYALRefChem:187004DTXCID60341824-H-3,5-DMBA205-167-5
Database identifiers
- CAS
134-96-3- PubChem CID
- 8655
- DTXSID
DTXSID2059643- ChEMBL
CHEMBL225303- ChEBI
CHEBI:67380- UNII
- 2ZR01KTT21
- EC Number
- 205-167-5
- Nikkaji
- J5.601D
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 157
Experimental & physicochemical properties
Solubility
Insoluble in water
Soluble (in ethanol)
Physical Description
Pale yellow solid; [Merck Index]
Very pale green needles; Alcoholic aroma
Kovats Retention Index
1652；1654；1617；1624.2；289.6
1670.3；1662；1669；1667；1643；1664；1670；1658；1662.8；1659.5
2934；2930；2904；2907.3
Physicochemical properties
- Melting point
- 110 · 110-113 °C(lit.)
- Boiling point
- 192 · 192-193 °C14 mm Hg(lit.)
- Density
- 1.013 · 1.013
- refractive index
- 1.45 · 1.4500 (estimate)
- FEMA
- 4049 · 4049 | 4-HYDROXY-3,5,-DIMETHOXY BENZALDEHYDE
- FLAVIS Number
- 5.153 · 05.153 | 4-Hydroxy-3,5-dimethoxybenzaldehyde
- Flash point
- 192 · 192-193°C/14mm
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Chloroform, Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 7.8 · 7.80±0.23(Predicted)
- color
- Light yellow-green to brown
- Odor
- 100 % · at 100.00 %. mild plastic woody tonka sweet
- Odor Type
- green
- biological source
- synthetic
- Water Solubility
- very sparingly soluble
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,9015
- JECFA Number
- 1878 · 1878
- BRN
- 784514 · 784514
- Henry's Law Constant
- 3.7 · 3.7×105 mol/(m3Pa) at 25℃, McFall et al. (2020)
- Stability
- Hygroscopic
- Major Application
- cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
- InChI
- 1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
- InChIKey
- KCDXJAYRVLXPFO-UHFFFAOYSA-N
- SMILES
- COc1cc(C=O)cc(OC)c1O
- LogP
- 1.3 · 1.30
- Substances Added to Food (formerly EAFUS)
- 4 · 4-HYDROXY-3,5-DIMETHOXYBENZALDEHYDE
- CAS DataBase Reference
- 134 · 134-96-3(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 ZR01KTT21 · 2ZR01KTT21
- NIST Chemistry Reference
- 4 · Benzaldehyde, 4-hydroxy-3,5-dimethoxy-(134-96-3)
- EPA Substance Registry System
- Syringaldehyde (134-96-3)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-37/39-36
- WGK Germany
- 3 · 3
- RTECS
- 5760000 · CU5760000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29124900 · 29124900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (> 99.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1484 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: Benzaldehyde, 4-hydroxy-3,5-dimethoxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 22-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23123
Benzaldehyde, 4-hydroxy-3,5-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes altered sleep time (including change in righting reflex) in intraperitoneal lethal-dose studies of mice (LD50 = 1,000 mg/kg); [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (97.6%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (> 99.9%)
Regulatory information
Regulatory Information
Chemical: Benzaldehyde, 4-hydroxy-3,5-dimethoxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 22-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23123
Benzaldehyde, 4-hydroxy-3,5-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CU5760000
- hs_code
- 29124900
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-37/39-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesWidely distributed in plants. [Merck Index] Used as flavoring agent or adjuvant; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing InformationBenzaldehyde, 4-hydroxy-3,5-dimethoxy-: ACTIVE
Applications
DescriptionSyringaldehyde is an important constituent of many plant isolates and has widespread occurrence in wood products. It can be easily converted to trimethoxy-benzaldehyde which is an essential intermediate of the antibacterial drug trimethoprim. It is also used in the colorimetric determination of free chlorine in water.
OccurrenceReported found in pineapple, beer, wine, grape brandy, rum, many different whisky products, sherry, roasted barley and hardwood smoke
UsesSyringaldehyde is used in biological studies for the isolation and structural characterization of milled wood lignin, dioxane lignin, and cellulolytic lignin preparation from Brewer''s spent grain.
UsesSyringaldehyde may be used as an analytical reference standard for the determination of the analyte in guacoextracts and pharmaceutical preparations,(1) cognacs and wines,(2) plum brandies,(4) and wheat straw(5) by various chromatography techniques.
General DescriptionSyringaldehyde is an aromatic phenolic aldehyde and a degradation product of lignin. It exhibits antioxidant activity and is reported to inhibit prostaglandin synthetase enzyme. The synthetic form of syringaldehyde is commercially used in pharmaceuticals, food, cosmetics, textiles, pulp and paper industries.
Preparation methods
PreparationVanillin is converted to 5-iodovanillin, which is treated with sodium methoxide to form 4-hydroxy-3,5- dimethyxybenzaldehyde.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.
Related reactions
115 records
Linked notes
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