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A p p e a r a n c e
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P a g e s f o r l o g g e d o u t e d i t o r s l e a r n m o r e ● C o n t r i b u t i o n s ● T a l k
( T o p )
1 N a t u r a l o c c u r r e n c e s
T o g g l e N a t u r a l o c c u r r e n c e s s u b s e c t i o n
1 . 1 I n f o o d
1 . 2 D e r i v a t i v e s
1 . 3 B i o s y n t h e s i s
1 . 4 B i o s y n t h e t i c b u i l d i n g b l o c k
2 S e e a l s o
3 R e f e r e n c e s
T o g g l e t h e t a b l e o f c o n t e n t s
p - C o u m a r i c a c i d
1 6 l a n g u a g e s
● Č e š t i n a ● D e u t s c h ● Ε λ λ η ν ι κ ά ● E s p a ñ o l ● E s p e r a n t o ● F r a n ç a i s ● I t a l i a n o ● N e d e r l a n d s ● 日 本 語 ● R o m â n ă ● Р у с с к и й ● S l o v e n č i n a ● С р п с к и / s r p s k i ● S r p s k o h r v a t s k i / с р п с к о х р в а т с к и ● S u o m i ● 中 文
E d i t l i n k s
● A r t i c l e ● T a l k
E n g l i s h
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T o o l s
T o o l s
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P r i n t / e x p o r t
● D o w n l o a d a s P D F ● P r i n t a b l e v e r s i o n
A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
( R e d i r e c t e d f r o m 4 - h y d r o x y c i n n a m i c a c i d )
p
Names
Preferred IUPAC name
(2 E
Other names
(E E para -Coumaric acid
Identifiers
CAS Number
3D model (JSmol )
Interactive image
Beilstein Reference
2207383
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.116.210
EC Number
Gmelin Reference
2245630
IUPHAR/BPS
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11 )12/h1-6,10H,(H,11,12)/b6-3+ Y
Key: NGSWKAQJJWESNS-ZZXKWVIFSA-N Y
InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11 )12/h1-6,10H,(H,11,
12)/b6-3+/f/h11H
InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11 )12/h1-6,10H,(H,11,12)/b6-3+
Key: NGSWKAQJJWESNS-ZZXKWVIFBJ
C1=CC(=CC=C1\C=C\C(=O)O)O
c1cc(ccc1/C=C/C(=O)O)O
Properties
Chemical formula
C 9 H 8 O 3
Molar mass
−1
Melting point
210 to 213 °C (410 to 415 °F; 483 to 486 K )
Hazards
GHS labelling
Pictograms
Signal word
Danger
Hazard statements
H301 , H302 , H311 , H314 , H315 , H317 , H319 , H335
Precautionary statements
P260 , P261 , P264 , P270 , P271 , P272 , P280 , P301+P310 , P301+P312 , P301+P330+P331 , P302+P352 , P303+P361+P353 , P304+P340 , P305+P351+P338 , P310 , P312 , P321 , P322 , P330 , P332+P313 , P333+P313 , P337+P313 , P361 , P362 , P363 , P403+P233 , P405 , P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
p organic compound with the formula HOC6 H 4 2 hydroxycinnamic acid . It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether .
Natural occurrences [ edit ]
It is a precursor to many natural products, especially lignols , precursors to the woody mass that comprise many plants.[1] p Gnetum cleistostachyum [2]
In food [ edit ]
p peanuts , navy beans, tomatoes , carrots , basil and garlic .[citation needed It is found in wine and vinegar .[3] barley grain.[4]
p pollen is a constituent of honey .[5]
Derivatives [ edit ]
p breads containing flaxseed .[6] p carnauba wax .
Biosynthesis [ edit ]
It is biosynthesized from cinnamic acid by the action of the P450 -dependent enzyme 4-cinnamic acid hydroxylase (C4H).
→
C 4 H
{\displaystyle {\begin{matrix}{}\\{\xrightarrow {\mathrm {C4H} }}\\{}\end{matrix}}}
It is also produced from L tyrosine by the action of tyrosine ammonia lyase (TAL).
→
T A L
{\displaystyle {\xrightarrow {\mathrm {TAL} }}}
3 +
Biosynthetic building block [ edit ]
p 4-ethylphenol produced by the yeast Brettanomyces cinnamate decarboxylase catalyzes the conversion of p 4-vinylphenol .[7] Vinyl phenol reductase then catalyzes the reduction of 4-vinylphenol to 4-ethylphenol. Coumaric acid is sometimes added to microbiological media , enabling the positive identification of Brettanomyces by smell.
The conversion of p Brettanomyces
cis -p uridine diphosphate glucose and cis -p 4 ′-O D cis -p uridine diphosphate (UDP). This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases.[8]
Phloretic acid , found in the rumen of sheep fed with dried grass, is produced by hydrogenation of the 2-propenoic side chain of p [9]
The enzyme, resveratrol synthase , also known as stilbene synthase, catalyzes the synthesis of resveratrol ultimately from a tetraketide derived from 4-coumaroyl CoA .[10]
p photoactive yellow proteins (PYP) , a homologous group of proteins found in many eubacteria.[11]
See also [ edit ]
References [ edit ]
^ Yao CS, Lin M, Liu X, Wang YH (April 2005). "Stilbene derivatives from Gnetum cleistostachyum". Journal of Asian Natural Products Research . 7 2 ): 131–7. doi :10.1080/10286020310001625102 . PMID 15621615 . S2CID 37661785 .
^ Gálvez MC, Barroso CG, Pérez-Bustamante JA (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung . 199 : 29–31. doi :10.1007/BF01192948 . S2CID 91784893 .
^ Quinde-Axtell Z, Baik BK (December 2006). "Phenolic compounds of barley grain and their implication in food product discoloration". Journal of Agricultural and Food Chemistry . 54 26 ): 9978–84. doi :10.1021/jf060974w . PMID 17177530 .
^ Mao W, Schuler MA, Berenbaum MR (May 2013). "Honey constituents up-regulate detoxification and immunity genes in the western honey bee Apis mellifera" . Proceedings of the National Academy of Sciences of the United States of America . 110 (22 ): 8842–6. Bibcode :2013PNAS..110.8842M . doi :10.1073/pnas.1303884110 PMC 3670375 PMID 23630255 .
^ Strandås C, Kamal-Eldin A, Andersson R, Åman P (October 2008). "Phenolic glucosides in bread containing flaxseed". Food Chemistry . 110 (4 ): 997–9. doi :10.1016/j.foodchem.2008.02.088 . PMID 26047292 .
^ "Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol" . etslabs.com . Archived from the original on 2008-02-19.
^ Rasmussen S, Rudolph H (1997). "Isolation, purification and characterization of UDP-glucose: cis -p D Phytochemistry . 46 3 ): 449–453. doi :10.1016/S0031-9422(97 )00337-3 .
^ Chesson A, Stewart CS, Wallace RJ (September 1982). "Influence of plant phenolic acids on growth and cellulolytic activity of rumen bacteria" . Applied and Environmental Microbiology . 44 3 ): 597–603. Bibcode :1982ApEnM..44..597C . doi :10.1128/aem.44.3.597-603.1982 . PMC 242064 PMID 16346090 .
^ Wang, Chuanhong; Zhi, Shuang; Liu, Changying; Xu, Fengxiang; Zhao, Aichun; Wang, Xiling; Ren, Yanhong; Li, Zhengang; Yu, Maode (2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea ) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli ". Journal of Agricultural and Food Chemistry . 65 8 ): 1659–1668. doi :10.1021/acs.jafc.6b05212 . PMID 28168876 .
^ Hoff WD, Düx P, Hård K, Devreese B, Nugteren-Roodzant IM, Crielaard W, Boelens R, Kaptein R, van Beeumen J, Hellingwerf KJ (November 1994). "Thiol ester-linked p . Biochemistry . 33 47 ): 13959–62. doi :10.1021/bi00251a001 . PMID 7947803 .
t
e
Aglycones
Precursor
Monohydroxycinnamic acids
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O
others
Esters
glycoside-likes
Esters of
Glycosides
Tartaric acid esters
Other esters
Caffeoyl phenylethanoid
Echinacoside
Calceolarioside A , B C F
Chiritoside A , B C
Cistanoside A , B C D E F G H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (Isoverbascoside , 2 ′-Acetylverbascoside
Oligomeric forms
Dimers
Diferulic acids (DiFA) : 5,5′-Diferulic acid , 8-O , 8,5′-Diferulic acid , 8,5′-DiFA (DC ) , 8,5′-DiFA (BF ) , 8,8′-Diferulic acid
Trimers
Tetramers
Conjugates withcoenzyme A (CoA)
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=P-Coumaric_acid&oldid=1117778845 " C a t e g o r i e s : ● H y d r o x y c i n n a m i c a c i d s ● V i n y l o g o u s c a r b o x y l i c a c i d s H i d d e n c a t e g o r i e s : ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e c o m p o u n d I D s ● M u l t i p l e c h e m i c a l s i n a n i n f o b o x t h a t n e e d i n d e x i n g ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A l l a r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s ● A r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s f r o m M a y 2 0 1 8
● T h i s p a g e w a s l a s t e d i t e d o n 2 3 O c t o b e r 2 0 2 2 , a t 1 4 : 4 7 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
