Compound: vanillin
SMILES: O=Cc1cc(OC)c(O)cc1
InChIKey: MWOOGOJBHIARFG-UHFFFAOYSA-N
Synonyms: vanillin, 4-Hydroxy-3-methoxybenzaldehyde, 121-33-5, Vanillic aldehyde, Vanillaldehyde, p-Vanillin, Vanilline, Lioxin, 3-Methoxy-4-hydroxybenzaldehyde, 4-Hydroxy-3-methoxy-benzaldehyde, 4-Hydroxy-m-anisaldehyde, 2-Methoxy-4-formylphenol, Benzaldehyde, 4-hydroxy-3-methoxy-, Zimco, p-Hydroxy-m-methoxybenzaldehyde, Methylprotocatechuic aldehyde, 4-Formyl-2-methoxyphenol, 4-Hydroxy-5-methoxybenzaldehyde, m-Anisaldehyde, 4-hydroxy-, Protocatechualdehyde, methyl-, Rhovanil, FEMA No. 3107, vaniline, Protocatechualdehyde 3-methyl ether, Oleoresin vanilla, m-Methoxy-p-hydroxybenzaldehyde, Vanillin Melting Point Standard, NSC-15351, NSC-48383, NSC-403658, DTXSID0021969, 4-hydroxy-3-methoxy-benzyldehyde, NPLC-0145, CHI530446X, DTXCID301969, CHEBI:18346, H-0264, NSC15351, Vanillin,, RefChem:6510, 204-465-2, Vanilla, Vanilin, Vanillin (natural), Vanillin (NF), NSC 15351, Vanillin [NF], Vanillin (Standard), MFCD00006942, CHEMBL13883, Vanillin-13C, 4-HYDROXY,3-METHOXY-BENZALDEHYDE, NCGC00091645-03, 4-hydroxy-3-methoxybenzaldehyde (vanillin), WLN: VHR DQ CO1, Vanillin [USAN], Vanilla oleoresin, CAS-121-33-5, CCRIS 2687, HSDB 1027, EINECS 204-465-2, BRN 0472792, UNII-CHI530446X, AI3-00093, Vanillin CRS, 3-methoxy-4-hydroxy-benzaldehyde, Vanillin, natural, Vanillin Essential, Vanillin ex Clove, oleo-Resins vanilla, V55, Vanillin - natural, Vanillin sodium salt, Vanillin (Rhovanil), Vanillin - synthetic, Vanillin M.P. RS, Vanillin (Rhovea(R)), VANILLIN [FHFI], VANILLIN [HSDB], oleo-Resins vanilla-bean, VANILLIN [FCC], VANILLIN [II], VANILLIN [MI], VANILLIN [VANDF], methyl-Protocatechualdehyde, VANILLIN [MART.], Vanillin (NIST) negative, Vanillin (NIST) positive, bmse000343, bmse000597, bmse010006, Methylprotcatechuic aldehyde, VANILLIN [USP-RS], VANILLIN [WHO-DD], EC 204-465-2, SCHEMBL1213, Vanillin Nat Ex ferulic acid, 4-08-00-01763 (Beilstein Handbook Reference), MLS002303069, BIDD:ER0330, SCHEMBL911154, Vanillin, puriss., 99.5%, GTPL6412, orb1300527, orb3140747, SCHEMBL7762777, SGCUT00016, 4-hydroxy 3-methoxybenzaldehyde, VANILLIN [EP MONOGRAPH], SCHEMBL28422417, SCHEMBL29354839, HY-N0098R, Vanilla oleoresin (vanilla SPP), 3-methoxy-4-hydroxy benzaldehyde, 4-hydroxy-3-methoxy benzaldehyde, VANILLIN, NATURAL [FHFI], 3-methoxy-4-hydroxy benzoaldehyde, Vanillin, ReagentPlus(R), 99%, 4-hydroxy-3-(methoxy)benzaldehyde, HMS3651D20, HMS3885K07, HMS5081K12, Vanillin, >=97%, FCC, FG, 4-hydoxy-3-(methyloxy)benzaldehyde, HY-N0098, LDA88484, NSC48383, STR01001, to_000089, Tox21_113534, Tox21_201925, Tox21_300352, 4-hydoxy-3-(methyloxy)benz aldehyde, BBL011956, BDBM50177405, EBC-12930, MSK3337-100M, NSC403658, s3071, SBB000108, STK199262, AKOS000118929, MSK3337-1000M, Tox21_113534_1, CCG-266230, CS-W020052, FV09779, RP10096, Vanillin, tested according to Ph.Eur., NCGC00091645-01, NCGC00091645-02, NCGC00091645-04, NCGC00091645-05, NCGC00091645-07, NCGC00254468-01, NCGC00259474-01, Vanillin, natural, >=97%, FCC, FG, AC-10370, BP-10602, FV156832, NCI60_001085, SMR000156285, ST052001, Vanillin 1000 microg/mL in Acetonitrile, Vanillin Solution in Methanol, 100ug/mL, Vanillin, JIS special grade, >=98.0%, Vanillin, Vetec(TM) reagent grade, 98%, 3-Methoxy-4-hydroxybenzaldehyde (vanillin), DB-003805, Vanillin Solution in Methanol, 1000ug/mL, CS-0694801, H0264, NS00009754, SW219190-1, V0080, EN300-18281, vanillin (3-methoxy-4-hydroxy- benzaldehyde), C00755, D00091, Q33495, 4-Hydroxy-3-methoxybenzaldehyde inclusion complex, Vanillin (83 degrees C) Melting Point Standard, 4-hydroxy-3-methoxy-Benzaldehyde-5-chlorovanillin, 4-hydroxy-3-methoxybenzaldehyde (ACD/Name 4.0), AC-907/21098004, F032468, BRD-K24258499-001-05-8, Vanillin, TraceCERT(R), certified reference material, Z57772449, 4-Hydroxy-3-Methoxybenzaldehyde; Eugenol EP Impurity H, F2190-0587, Vanillin, European Pharmacopoeia (EP) Reference Standard, Mettler-Toledo Calibration substance ME 51143093, Vanillin, Vanillin, United States Pharmacopeia (USP) Reference Standard, Vanillin, Pharmaceutical Secondary Standard; Certified Reference Material, InChI=1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H, Vanillin Melting Point Standard, United States Pharmacopeia (USP) Reference Standard, Mettler-Toledo Calibration substance ME 51143093, Vanillin, traceable to primary standards (LGC), Vanillin melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C8H8O3
molecular_weight: 152.15 g/mol
exact_mass: 152.047344113 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 11
topological_polar_surface_area: 46.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White crystalline needles from water
color: White crystalline needles from water
odor: Sweetish smell
boiling_point: 545 °F at 760 mmHg (NTP, 1992)
melting_point: 178 to 181 °F (NTP, 1992)
density: 1.056 at 68 °F (NTP, 1992) - Denser than water; will sink
solubility: Slightly soluble (NTP, 1992)
flash_point: 153 °C (307 °F) - closed cup
vapor_pressure: 1 mmHg at 225 °F (NTP, 1992)
Descriptions:
{"pubchem": "Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. It has a role as an antioxidant, a flavouring agent, an anticonvulsant, an anti-inflammatory agent and a plant metabolite. It is a member of benzaldehydes, a monomethoxybenzene and a member of phenols.", "chebi": "A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively.", "chembl": "VANILLIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.", "wikipedia": "Vanillin is an organic compound with the molecular formula C8H8O3.  It is a phenolic aldehyde.  Its functional groups include aldehyde, hydroxyl, and ether.  It is the primary component of the ethanolic extract of the vanilla bean.  Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.\nVanillin and ethylvanillin are used by the food industry;  ethylvanillin is more expensive, but has a stronger note. It differs from vanillin by having an ethoxy group (\u2212O\u2212CH2CH3) instead of a methoxy group (\u2212O\u2212CH3).\nNatural vanilla extract is a mixture of several hundred different compounds in addition to vanillin.  Artificial vanilla flavoring is often an ethanol solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla,  synthetic preparation of artificial vanilla flavoring has long been of interest.  The first commercial synthesis of vanillin began with the more readily available natural compound eugenol (4-allyl-2-methoxyphenol).  Today, artificial vanillin is made either from guaiacol or lignin.\nLignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than that from guaiacol-based artificial vanilla; the difference is due to the presence of acetovanillone, a minor component in the lignin-derived product that is not found in vanillin synthesized from guaiacol."}