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2D Structure
Also known as: Trans-cinnamaldehyde, 104-55-2, 14371-10-9, Cinnamic aldehyde, 3-phenylacrylaldehyde, Cinnamal
Molecular Formula
C9H8O
Molecular Weight
132.16  g/mol
InChI Key
KJPRLNWUNMBNBZ-QPJJXVBHSA-N
FDA UNII
SR60A3XG0F

Cinnamaldehyde is a metabolite found in or produced by Saccharomyces cerevisiae.
Cinnamaldehyde is a Standardized Chemical Allergen. The physiologic effect of cinnamaldehyde is by means of Increased Histamine Release, and Cell-mediated Immunity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(E)-3-phenylprop-2-enal
2.1.2 InChI
InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
2.1.3 InChI Key
KJPRLNWUNMBNBZ-QPJJXVBHSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C=CC=O
2.1.5 Isomeric SMILES
C1=CC=C(C=C1)/C=C/C=O
2.2 Other Identifiers
2.2.1 UNII
SR60A3XG0F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-phenyl-2-propenal

2. 3-phenylprop-2-enaldehyde

3. Beta-phenylacrolein

4. Cinnamic Aldehyde

5. Cinnamic Aldehyde, (e)-isomer

6. Supercinnamaldehyde

7. Trans-3-phenylprop-2-enaldehyde

8. Trans-cinnamaldehyde

2.3.2 Depositor-Supplied Synonyms

1. Trans-cinnamaldehyde

2. 104-55-2

3. 14371-10-9

4. Cinnamic Aldehyde

5. 3-phenylacrylaldehyde

6. Cinnamal

7. (e)-cinnamaldehyde

8. Zimtaldehyde

9. 2-propenal, 3-phenyl-

10. 3-phenylpropenal

11. Phenylacrolein

12. (2e)-3-phenylprop-2-enal

13. (e)-3-phenylprop-2-enal

14. Trans-cinnamic Aldehyde

15. Cinnamylaldehyde

16. (e)-3-phenylpropenal

17. (e)-3-phenyl-2-propenal

18. Cassia Aldehyde

19. 3-phenylacrolein

20. 3-phenyl-2-propenal

21. Cinnemaldehyde

22. 2-propenal, 3-phenyl-, (2e)-

23. Cinnamyl Aldehyde

24. Abion Ca

25. Cinnamaldehyde, (e)-

26. Trans-cinnamylaldehyde

27. Benzylideneacetaldehyde

28. Beta-phenylcrolein

29. 3-phenyl-2-propenaldehyde

30. Acrolein, 3-phenyl-

31. 3-fenylpropenal

32. Fema No. 2286

33. 3-phenyl-2-propen-1-al

34. Trans-3-phenyl-2-propenal

35. (e)-cinnamic Aldehyde

36. 3-phenylprop-2-enal

37. Nci-c56111

38. 2-propenal, 3-phenyl-, (e)-

39. (2e)-3-phenylacrylaldehyde

40. .beta.-phenylacrolein

41. Chebi:16731

42. Cinnamaldehyde, Trans-

43. (e)-3-phenyl-propenal

44. Mfcd00007000

45. Nsc-16935

46. Nsc-40346

47. Sr60a3xg0f

48. (3e)-3-phenylprop-2-enal

49. (2e)-3-phenyl-2-propenal

50. Chembl293492

51. Aldehyd Skoricovy

52. Xc-800

53. Ncgc00091512-04

54. Nsc 16935

55. Dsstox_cid_4834

56. Wln: Vh1u1r

57. Dsstox_rid_77548

58. Dsstox_gsid_24834

59. Caswell No. 221a

60. Fema Number 2286

61. 3-fenylpropenal [czech]

62. Aldehyd Skoricovy [czech]

63. Cinnamic Aldehyde (natural)

64. Hefty Dog And Cat Repellent

65. Cas-14371-10-9

66. Ccris 3189

67. Ccris 6222

68. Cinnamaldehyde [nf]

69. Hsdb 209

70. Einecs 203-213-9

71. Unii-sr60a3xg0f

72. Epa Pesticide Chemical Code 040506

73. Brn 0605737

74. Brn 1071571

75. E-cinnamaldehyde

76. Ai3-00473

77. Ai3-33275

78. Transcinnamaldehyde

79. Trans Cinnamaldehyde

80. Nat. Cinnamaldehyde

81. Cnma

82. (trans)-cinnamaldehyde

83. Trans Cinnamic Aldehyde

84. Trans-3-phenylacrolein

85. Cinnamaldehyde, Natural

86. Cinnamal [inci]

87. Trans-3-phenyl-propenal

88. (e)-phenylvinyl Aldehyde

89. (e)-3-phenylacrylaldehyde

90. Bmse010257

91. Epitope Id:150921

92. Cinnamaldehyde [ii]

93. Cinnamaldehyde [mi]

94. Ec 203-213-9

95. Trans-3-phenylacrylaldehyde

96. Trans-cinnamaldehyde ,(s)

97. Schembl3441

98. Trans-cinnamaldehyde, 99%

99. (e)-3-phenyl-acrylaldehyde

100. Cinnamaldehyde [fcc]

101. Trans-cinnamaldehyde; Trans-3-phenylacrylaldehyde

102. Cinnamaldehyde (trans), Neat

103. Cinnamaldehyde [fhfi]

104. Cinnamaldehyde [hsdb]

105. 2-07-00-00273 (beilstein Handbook Reference)

106. 4-07-00-00984 (beilstein Handbook Reference)

107. Mls002454394

108. Cinnamaldehyde (trans)

109. Trans-cinnamaldehyde, >=99%

110. Gtpl2423

111. (e)-cinnamaldehyde (incorrect)

112. Cinnamaldehyde [usp-rs]

113. Cinnamaldehyde [who-dd]

114. Natural Cinnamic Aldehyde

115. Dtxsid6024834

116. Trans-cinnamaldehyde (incorrect)

117. Chebi:142921

118. Hms2268o08

119. Hms3885e04

120. Hy-n0609

121. Nsc16935

122. Nsc40346

123. Zinc1532777

124. Tox21_111144

125. Tox21_201804

126. Tox21_303271

127. Bdbm50203065

128. S3763

129. Stk397371

130. Akos000119171

131. Cinnamaldehyde, Natural, >=95%, Fg

132. Ccg-266119

133. Db14184

134. Cinnamaldehyde Min. 98%, For Synthesis

135. Cinnamaldehyde 100 Microg/ml In Toluene

136. Ncgc00091512-01

137. Ncgc00091512-02

138. Ncgc00091512-05

139. Ncgc00091512-06

140. Ncgc00091512-07

141. Ncgc00257017-01

142. Ncgc00259353-01

143. Trans-cinnamaldehyde, Analytical Standard

144. As-12078

145. As-75456

146. Smr000112334

147. Trans-cinnamaldehyde, >=98%, Fcc, Fg

148. (e)-3-phenyl-2-propenal(e)-cinnamaldehyde

149. Db-003796

150. Am20060482

151. Cs-0009609

152. N1482

153. A14480

154. C00903

155. Cinnamaldehyde, Vetec(tm) Reagent Grade, 93%

156. D72477

157. A801001

158. Q204036

159. W-205597

160. B99dd6c7-1c6d-4fe3-a172-54bfdb987683

161. Cinnamaldehyde (constituent Of Cinnamomum Verum Bark) [dsc]

162. Cinnamaldehyde, United States Pharmacopeia (usp) Reference Standard

163. Trans-cinnamaldehyde (constituent Of Cinnamomum Cassia Bark) [dsc]

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 132.16 g/mol
Molecular Formula C9H8O
XLogP31.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass132.057514874 g/mol
Monoisotopic Mass132.057514874 g/mol
Topological Polar Surface Area17.1 Ų
Heavy Atom Count10
Formal Charge0
Complexity121
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ Cinnamonum zeylanicum (cinnamon) is widely used in traditional system of medicine to treat diabetes in India. The present study was carried out to isolate and identify the putative antidiabetic compounds ... Cinnamaldehyde was administered at different doses (5, 10 and 20 mg/kg bw) for 45 days to streptozotocin (STZ) (60 mg/kg bw)-induced male diabetic wistar rats. It was found that plasma glucose concentration was significantly (p<0.05) decreased in a dose-dependent manner (63.29%) compared to the control. In addition, oral administration of cinnamaldehyde (20 mg/kg bw) significantly decreased glycosylated hemoglobin (HbA(1C)), serum total cholesterol, triglyceride levels and at the same time markedly increased plasma insulin, hepatic glycogen and high-density lipoprotein-cholesterol levels. Also cinnamaldehyde restored the altered plasma enzyme (aspartate aminotransferase, alanine aminotransferase, lactate dehydrogenase, alkaline phosphatase and acid phosphatase) levels to near normal. Administration of glibenclamide, a reference drug (0.6 mg/kg bw) also produced a significant (p < 0.05) reduction in blood glucose concentration in STZ-induced diabetic rats. The results of this experimental study indicate that cinnamaldehyde possesses hypoglycemic and hypolipidemic effects in STZ-induced diabetic rats.

PMID:17140783 Subash BP et al; Phytomedicine 14 (1): 15-22 (2007).


4.2 Minimum/Potential Fatal Human Dose

The probable oral lethal dose for humans is 0.5 to 5 g/kg for a 70-kg person. Both the oil and pure aldehyde are irritants, especially if undiluted. They can also cause inflammation and erosion of gastrointestinal mucosa. Prolonged skin contact (more than 48 hr) can produce superficial partial thickness burns

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 1048


3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-256


4.3 Drug Indication

Cinnamaldehyde is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antimutagenic Agents

Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved. (See all compounds classified as Antimutagenic Agents.)


Flavoring Agents

Substances added to foods and medicine to improve the taste. (See all compounds classified as Flavoring Agents.)


Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
CINNAMALDEHYDE
5.2.2 FDA UNII
SR60A3XG0F
5.2.3 Pharmacological Classes
Chemical Structure [CS] - Allergens
5.3 Absorption, Distribution and Excretion

Absorption

Cinnamaldehyde is 52% absorbed through the skin and shown to be rapidly absorbed from the gut.


Route of Elimination

Cinnamaldehyde is metabolized and excreted primarily in the urine and, to a minor extent, in the feces. After oral or intraperitoneal administration to rats and mice, 6998% of the dose of cinnamaldehyde was recovered in the urine and feces within 24 h.


The bioavailability of microencapsulated cinnamaldehyde (CNMA) was investigated in male F344 rats. Rats were gavaged with CNMA in corn oil using either microencapsulated or the neat chemical at doses of 50, 250, and 500 mg/kg. No differences between the two formulations at any of the doses were found in either CNMA blood concentration profiles or in the rate of urinary hippuric acid excretion. Both formulations showed a low bioavailability (< 20%) at 250 and 500 mg/kg. Regardless of the formulation used, oral gavage of CNMA significantly increased the urinary excretion of hippuric acid. About 75% of the dose of CNMA was metabolized to hippuric acid and recovered in the urine. The total amount of hippuric acid recovered in a 50-hr urinary collection correlated well with the CNMA dose. The data suggest that there was complete release of CNMA from the microcapsules and that microencapsulation of CNMA does not affect its bioavailability or its metabolism ...

PMID:8432430 Yuan J et al; Fundam Appl Toxicol 20 (1): 83-7 (1993).


/Cinnamaldehyde is/ presumably oxidized in vivo to cinnamic acid, which is excreted in urine as benzoic and hippuric acids.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-256


After ip admin of cinnamic aldehyde to rats, urinary thio ether excretion amounted to 6.5% of dose.

DELBRESSINE LP C ET AL; BR J PHARMACOL 68 (1): 165 (1980)


Cinnamaldehyde administered intraperitoneally to a rabbit was excreted in the urine as cinnamic acid, cinnamoylglycine, benzoic acid and hippuric acid.

WHO/FAO; Joint Expert Committee on Food Additives (JECFA) - Monographs and Evaluations; Food Additive Series 14: Cinnamaldehyde (1981). Available from database query, as of July 13, 2009: https://www.inchem.org/pages/jecfa.html


For more Absorption, Distribution and Excretion (Complete) data for CINNAMALDEHYDE (7 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

The metabolism of trans-[3-14C]cinnamaldehyde was investigated in male and female Fischer 344 rats and CD1 mice at doses of 2 and 250 mg/kg bw given by ip injection and in males at 250 mg/kg by oral gavage. Some 94% of the administered dose was recovered in the excreta in 72 hr in both species with most (75-81%) present in the 0-24-hr urine. Less than 2% of the administered dose was found in the carcasses at 72 hr after dosing. Urinary metabolites were identified by their chromatographic characteristics. In both species the major urinary metabolite was hippuric acid accompanied by 3-hydroxy-3-phenylpropionic acid, benzoic acid and benzoyl glucuronide. The glycine conjugate of cinnamic acid was formed to a considerable extent only in the mouse. The oxidative metabolism of cinnamaldehyde essentially follows that of cinnamic acid, by beta-oxidation analogous to that of fatty acids. Apart from the metabolites common to cinnamic acid and cinnamaldehyde, 7% of 0-24-hr urinary 14C was accounted for by two new metabolites in the rat and three in the mouse, which have been shown in other work to arise from a second pathway of cinnamaldehyde metabolism involving conjugation with glutathione. The excretion pattern and metabolic profile of cinnamaldehyde in rats and mice are not systematically affected by sex, dose size and route of administration. The data are discussed in terms of their relevance to the safety evaluation of trans-cinnamaldehyde, particularly the validity or otherwise of extrapolation of toxicity data from high to low dose. /trans-Cinnamaldehyde/

PMID:7959441 Peters MM, Caldwell J; Food Chem Toxicol 32 (10): 869-76 (1994).


To evaluate the extent of cinnamaldehyde and cinnamic alcohol metabolism in human skin and provide evidence for the role of cutaneous alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) in such metabolism ... the extent of cinnamic alcohol and aldehyde metabolism was investigated in human skin homogenates and sub-cellular fractions ... Studies were conducted in the presence and absence of the ADH/cytochrome P450 inhibitor 4-methylpyrazole and the cytosolic ALDH inhibitor, disulfiram. Differential metabolism of cinnamic alcohol and cinnamaldehyde was observed in various subcellular fractions: skin cytosol was seen to be the major site of cinnamic compound metabolism. Significant metabolic inhibition was observed using 4-methylpyrazole and disulfiram in whole skin homogenates and cytosolic fractions only ... This study has demonstrated that cutaneous ADH and ALDH activities, located within defined subcellular compartments, play important roles in the activation and detoxification of CAlc and CAld in skin ...

PMID:12615359 Cheung C et al; J Dermatol Sci 31 (1): 9-19 (2003).


Cinnamaldehyde administered intraperitoneally to a rabbit was excreted in the urine as cinnamic acid, cinnamoylglycine, benzoic acid and hippuric acid.

WHO/FAO; Joint Expert Committee on Food Additives (JECFA) - Monographs and Evaluations; Food Additive Series 14: Cinnamaldehyde (1981). Available from database query, as of July 13, 2009: https://www.inchem.org/pages/jecfa.html


Identification of 2 sulfur containing urinary metabolites of cinnamic aldehyde in rat which are 3-S-(N-acetylcysteinyl)-3-phenylpropyl alcohol and 3-S-(N-acetylcysteinyl)-3-phenylpropionic acid.

DELBRESSINE LP C ET AL; BR J PHARMACOL 68 (1): 165 (1980)


For more Metabolism/Metabolites (Complete) data for CINNAMALDEHYDE (6 total), please visit the HSDB record page.


Cinnamaldehyde is a known human metabolite of cinnarizine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560