Cinnamic aldehyde

Manufactured by Merck Group

Sourced in Germany

Cinnamic aldehyde (CA) is a clear, colorless to pale yellow liquid chemical compound. It is the primary constituent of cinnamon oil and has a characteristic sweet, cinnamony aroma. CA is commonly used as a flavoring agent and in the production of other chemicals.

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Cinnamic (11 citations)

6 protocols using cinnamic aldehyde

Fluorescence-based Oxidative Stress Assay

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CA, CAAE,
CAPE, cinnamic aldehyde, sodium phosphate monobasic monohydrate (NaH₂PO₄ H₂O), sodium phosphate dibasic heptahydrate
(Na₂HPO₄ 7H₂O), 1,1-diphenyl-2-picrylhydrazyl
radical (DPPH), NaIO₄, KIO₄, 2,4-dinitrochlorobenzene
(DNCB), and N-acetylcysteine (NAC) were purchased
from Sigma-Aldrich (Steinheim, Germany). Deuterated NMR solvents were
acquired from Cambridge Isotope Laboratories. Ethanol (EtOH) (96%)
and formic acid (FA) (99–100%) were obtained from VWR International
(Pennsylvania, US). Acetonitrile (ACN) (≥99.9%), LC-grade water,
and the 2 mL deep-well plates were acquired from Thermo Fisher Scientific
(Seelze, Germany). N-Terminal acetylated peptide Ac-PHCKRM was obtained
from Peptide 2.0 (Chantilly, US), while Ac-RFAACAA was acquired from
RS Synthesis (Louisville, United States). Monobromobimane (MBrB) was
purchased from Cayman Chemical (Michigan, United States). 96-well
black plates were purchased from PerkinElmer (Massachusetts, United
States).

Ndreu L., Hurben A.K., Nyman G.S., Tretyakova N.Y., Karlsson I, & Hagvall L. (2023). Investigation into Propolis Components Responsible for Inducing Skin Allergy: Air Oxidation of Caffeic Acid and Its Esters Contribute to Hapten Formation. Chemical Research in Toxicology, 36(6), 859-869.

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Allergy-Inducing Chemicals Protocol

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4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one (oxazolone), 2,4dinitrochlorobenzene, acetaminophen, 3-aminophenol, cinnamic aldehyde, iso eugenol, citral, tetramethylthiuram disulfide, 2-methoxy-4-methylphenol, resorcinol, eugenol, geraniol, cinnamic alcohol, benzalkonium chloride, vanillin, lactic acid, N,N-diethyl-3-methylbenzamide and 4-aminoacetanilide were obtained from Sigma Aldrich (Taufkirchen, Germany), whereas N,N'-bis(4-aminophenyl)-2,5-diamino-1,4-quinone-diimine (Bandrowski's base) was purchased from ICN Biomedicals (Aurora, OH, USA). Sodium dodecyl sulfate and dimethyl sulfoxide (DMSO) were purchased from Carl Roth (Karlsruhe, Germany). 4-Acetamidoacetanilide was synthesized as described (Kawakubo et al., 2000) . 4-Amino-2-methyl-acetanilide, 4-amino-3-methyl-acetanilide and 2,5-diacetaminotoluene were kind gifts from C. Goebel (P&G, Darmstadt, Germany).

Hennen J, & Blömeke B. (2017). Keratinocytes improve prediction of sensitization potential and potency of chemicals with THP-1 cells. ALTEX, 34(2).

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UPLC Analysis of Cinnamic Compounds

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The ACQUITY UPLC system (Waters Corp., Milford, MA, USA), controlled by Waters Empower 2 software, included a binary solvent manager, sampler manager, heated column compartment, photodiode array detector, single quadrupole detector, and a C18 column (1.7 μm, 2.1 × 100 mm). The column and sample temperatures were maintained at 40 °C and 25 °C, respectively. The elution gradient was as described^{16 (link)}, that is, the isocratic mobile phase was 10% (v/v) aqueous acetonitrile, and the flow rate was 0.8 mL/min. The detection wavelength was 280 nm. Cinnamic aldehyde (CA) and cinnamic acid (CAC) used as standards were purchased from Sigma-Aldrich and stored at −20 °C.

Wen T.C., Li Y.S., Rajamani K., Harn H.J., Lin S.Z, & Chiou T.W. (2018). Effect of Cinnamomum osmophloeum Kanehira Leaf Aqueous Extract on Dermal Papilla Cell Proliferation and Hair Growth. Cell Transplantation, 27(2), 256-263.

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Synthesis and Characterization of Acetophenone Azine

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Acetophenone Azine; Chemical name: 1‐phenyl‐ethanone(1‐phenylethylidene)hydrazine (CAS no. 729‐43‐1; batch number: 10138845 l) were purchased from Alfa Aesar and the purity of the compound was 97%; Cinnamic aldehyde (CA), (CAS no.14371‐10‐9) and dimethylsulfoxide (DMSO) were purchased from Sigma‐Aldrich. 2,4‐Dinitrochlorobenzene (DNCB) (CAS no.97‐00‐7) and Nickel Sulphate (NiSO₄) (CAS no.10101‐97‐0) were purchased from Sigma‐Aldrich and Merck, respectively. The purity of the compounds was reported equal to or higher than 99% by the respective suppliers.
Acetone:Olive oil 4:1 (vol/vol) mixture, N,N‐dimethylformamide (DMF), methyl ethyl ketone, propylene glycol, dimethyl sulfoxide and 1% aqueous Pluronic PE9200 were used as standard OECD vehicles.
α‐Hexylcinnamaldehyde (HCA) (CAS no.101‐86‐0; batch number: MKCD2910) was purchased from Sigma‐Aldrich Co.

Manière I., Aubert A., Dubois C., Solal C., Lepoittevin J, & Rousselle C. (2022). Sensitization properties of acetophenone azine, a new skin sensitizer identified in textile. Contact Dermatitis, 88(1), 35-42.

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Cinnamic Aldehyde and Sulforaphane Cytotoxicity

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Cinnamic aldehyde (CA) (C80687; Sigma-Aldrich, St. Louis, MO). DMEM (11885-084; Gibco, Grand Island, NY). DMSO (BP231; Thermo-Fisher Scientific, Waltham, MA). F-12 (11765-054; Gibco). Glucose (50-99-7, Sigma-Aldrich). Heat-inactivated fetal bovine serum (FBS) (16140071; Gibco). Paraformaldehyde (158127; Sigma-Aldrich). PBS (20–134; Apex Bioresearch Products, San Diego, CA). Sulforaphane (SFN) (S6317; Sigma-Aldrich). Trypsin-EDTA (0.05%) (25300054; Gibco).

Buglak N.E., Jiang W, & Bahnson E.S. (2018). Cinnamic aldehyde inhibits vascular smooth muscle cell proliferation and neointimal hyperplasia in Zucker Diabetic Fatty rats. Redox Biology, 19, 166-178.

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Fluorescent Labeling Techniques in Biomedical Research

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Synperonic^® PE/Pluronic P84 (P84,713538), Pluronic^® F-127 (F127, P2443), (Sigma-Aldrich, St. Louis, MO, USA), Poloxamer 331/Pluronic^® L101 (P1608) (Spectrum Chemical, Gardena, CA, USA). Nile red (N0659, TCI America, Portland, OR, USA), cinnamic aldehyde (CA) (C80687; Sigma-Aldrich, St. Louis, MO, USA), Rhodamine 123 (83702, Sigma-Aldrich, St. Louis, MO, USA), DiD (1,1′-Dioctadecyl-3,3,3′,3′-Tetramethylindodicarbocyanine Perchlorate) (D307, Thermo-Fisher, Waltham, MA, USA), (MTT) 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (L11939, Alfa Aesar, Haverhill, MA, USA).

Cartaya A.E., Lutz H., Maiocchi S., Nalesnik M, & Bahnson E.M. (2021). Delivery of Cinnamic Aldehyde Antioxidant Response Activating nanoParticles (ARAPas) for Vascular Applications. Antioxidants, 10(5), 709.

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