Basic information
- Standard SMILES
O=Cc1ccc(O)cc1- InChIKey
RGHHSNMVTDWUBI-UHFFFAOYSA-N- Molecular formula
- C7H6O2
- Average molar mass
- 122.12 g/mol
- Monoisotopic mass
- 122.03677943
Names & identifiers
- Preferred name
- 4-Hydroxybenzaldehyde
- IUPAC
- 4-hydroxybenzaldehyde
- English name
- 4-Hydroxybenzaldehyde
- Molecular formula
- C7H6O2
- Molecular weight
- 122.12
Names & synonyms
4-hydroxybenzaldehydep-Hydroxybenzaldehyde123-08-04-Formylphenolp-FormylphenolBenzaldehyde, 4-hydroxy-p-OxybenzaldehydeParahydroxybenzaldehydePara-HydroxybenzaldehydeNSC-2127O1738X3Y38DTXSID8059552
Show more names
PHBPARA HYDROXY BENZALDEHYDEFEMA 39844-Hydroxybenzaldehyde ,99%Hydroxy benzaldehyd
FEMA NO. 3984CHEBI:17597RefChem:99272DTXCID7033787204-599-14-Hydroxy benzaldehyde4-HYDROXY-BENZALDEHYDEBenzaldehyde, p-hydroxy-
Database identifiers
- CAS
123-08-0- PubChem CID
- 126
- DTXSID
DTXSID8059552- ChEMBL
CHEMBL14193- ChEBI
CHEBI:17597- UNII
- O1738X3Y38
- EC Number
- 204-599-1
- Nikkaji
- J1.156.979J、J43.312H
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 93
Experimental & physicochemical properties
LogP
1.35
1.35
LogS-0.96
Solubility
8450
8.45 mg/mL at 25 °C
slightly soluble in water; soluble in organic solvents
freely soluble (in ethanol)
Boiling Point
310
310.00 to 311.00 °C. @ 760.00 mm Hg
Melting Point
117
117 °C
Physical Description
Dry Powder
Solid; Sublimes at atmospheric pressure without decomposition; [Merck Index] Light brown crystalline solid; [Aldrich MSDS]
Solid
Beige powder; vanillic/nutty odour
Ionization Efficiency
Positive
1.13
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Dissociation Constants7.61 (at 25 °C)
Kovats Retention Index
1311；1317；1308；1318；1324；1318.6；1320.8；1320；1302；1318；1320；1323；1320；1313.5
2958
Collision Cross Section
122.34 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
118.2 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
121.6 Ų [M-H]-
Physicochemical properties
- Melting point
- 112 · 112-116 °C (lit.)
- Boiling point
- 191 °C · 191°C 50mm
- Density
- 1 · 1,129 g/cm3
- vapor pressure
- 0.004 Pa · 0.004Pa at 25℃
- refractive index
- 1.5105 · 1.5105 (estimate)
- FEMA
- 3984 · 3984 | 4-HYDROXYBENZALDEHYDE
- FLAVIS Number
- 5.047 · 05.047 | 4-Hydroxybenzaldehyde
- Flash point
- 174 °C · 174°C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 13.8 g/l · 13.8g/l
- form
- Crystalline Powder
- pka
- 7.61 · 7.61(at 25℃)
- color
- light yellow to light brown
- Odor
- 100 % · at 100.00 %. sweet nutty almond balsam woody
- Odor Type
- woody
- biological source
- synthetic
- Water Solubility
- 13 g/L · 13 g/L (30 ºC)
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,4811
- JECFA Number
- 956 · 956
- BRN
- 471352 · 471352
- Henry's Law Constant
- 1.9 · 1.9×104 mol/(m3Pa) at 25℃, Parsons et al. (1971)
- Stability
- Hygroscopic
- Major Application
- cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
- Cosmetics Ingredients Functions
- FRAGRANCEPERFUMING
- InChI
- 1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
- InChIKey
- RGHHSNMVTDWUBI-UHFFFAOYSA-N
- SMILES
- [H]C(=O)c1ccc(O)cc1
- LogP
- 1.3 at · 1.3 at 23℃
- CAS DataBase Reference
- 123 · 123-08-0(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 4 · 4-HYDROXYBENZALDEHYDE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1738 X3Y38 · O1738X3Y38
- NIST Chemistry Reference
- 4 · Benzaldehyde, 4-hydroxy-(123-08-0)
- EPA Substance Registry System
- p-Hydroxybenzaldehyde (123-08-0)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 318 · H318
- Precautionary statements
- 280 · P280-P305+P351+P338
- target organs
- Respiratory system
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-R36/37/38
- Safety Statements
- 26 · 26-36-24/25-37/39-S24/25
- WGK Germany
- 2 · 2
- RTECS
- 6475000 · CU6475000
- Autoignition Temperature
- 450 °C · 450 °C
- Hazard Note
- Irritant/Air Sensitive
- TSCA
- TSCA listed
- HS Code
- 29124900 · 29124900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 STOT · Eye Dam. 1STOT SE 3
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2250 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Not Classified；Reported as not meeting GHS hazard criteria by 1430 of 1647 companies
Aggregated GHS information provided per 1647 reports by companies from 13 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 1430 of 1647 reports by companies.；There are 12 notifications provided by 217 of 1647 reports by companies with hazard statement code(s).；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-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzaldehyde, 4-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 4-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 23-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/26915；Status: Active Update: 13-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18740
4-Hydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Aldrich MSDS]
Hazard Classes and CategoriesNot Classified
Regulatory information
Regulatory Information
Chemical: Benzaldehyde, 4-hydroxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzaldehyde, 4-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 4-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 23-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/26915；Status: Active Update: 13-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18740
4-Hydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- CU6475000
- hs_code
- 29124900
- Toxicity
- LD50 orally in Rabbit: 2250 mg/kg
- risk_code
- 36/37/38-R36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- hazard_note
- Irritant/Air Sensitive
- safety_code
- 26-36-24/25-37/39-S24/25
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H318
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1STOT SE 3
- Autoignition Temperature
- 450 °C
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesPresent in many plants in small amounts; [Merck Index] Used as flavoring agent or adjuvant; [FDA] Used to make pharmaceuticals; [Hawley]
U.S. Production2023: 87,300 lb；2022: 31,800 lb；2021: 71,400 lb；2020: 63,500 lb
Industry UsesIntermediate
Use Classification
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 Information
All Other Basic Organic Chemical Manufacturing
Benzaldehyde, 4-hydroxy-: ACTIVE
Applications
Uses1. It can be used for the synthesis of organic compounds and medicine. 2. The good is also the intermediate of the pharmaceutical, perfume, and liquid crystal. p-Hydroxybenzaldehyde can be used for the production of TMP (trimethoprim), amoxicillin, cefadroxil cephalosporins, artificial gastrodin, farrerol, bezafibrate, and esmolol; it can also be used for the production of perfume anisaldehyde, vanillin, ethyl vanillin, and raspberry ketone.3. It is the key raw material for the production of p-hydroxy phenylglycine (p-hydroxy phenylglycine is the key intermediate of the new generation of semi-synthetic penicillin amoxicillin). It is also the key intermediate raw material of the production of pesticides-bromoxynil.4. p-Hydroxybenzaldehyde（4-Hydroxybenzaldehyde,123-08-0） is an important intermediate of the pharmaceutical industry and the perfume industry.5. It is an important intermediate of medicine, perfume, and pesticides for the synthesis of drugs like hydroxyl ampicillin, trimethoprim, and 3-methoxy benzaldehyde. It can also used for synthesizing polymers and producing pharmaceutical raw materials.
OccurrenceIt is found as a volatile in several food products, including cherries, grapes, papayas, tomatoes, cheese, beer, rum, brandy, wine, tea and peanuts. Occurs in the form of esters in several plants, notably in wintergreen leaves and the bark of sweet birch.
Uses4-Hydroxybenzaldehyde maintains bactericidal activity when tested against certain bacteria strains. It also displays antioxidant potential when analyzed through assay. It is widely used starting material for polymers and pharmaceuticals.
General Description4-hydroxybenzaldehyde occurs naturally in vanilla beans and is one of the keys contributors to the vanilla flavor.
Preparation methods
Preparationp-Hydroxybenzaldehyde is prepared by heating sodium phenolate with carbon dioxide under pressure.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor.
Related reactions
1,589 records
Linked notes
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