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Profa. dra. Édira Castello Branco de Andrade Gonçalves
http://www.unirio.br/analisedealimentos
Carbohydrate
Carbohydrate
http://www.unirio.br/analisedealimentos
http://chemistry2.csudh.edu/rpendarvis/hemiacetal.html
Formation
Ketone
http://butane.chem.uiuc.edu/pshapley/GenChem2/B5/2.html
GLUCOSE
Carbohydrate
http://www.unirio.br/analisedealimentos
Formation sucrose
http://butane.chem.uiuc.edu/pshapley/GenChem2/B10/1.html
Condensation is the loss of
water in a chemical reaction
aldehyde
ketone
1,2 glycosidic bond
Carbohydrate
http://www.unirio.br/analisedealimentos
Formation maltose
aldehydeCondensation
Lobry de Bruyn–van Ekenstein transformation
pH, T
1,4 glycosidic bond
https://en.wikipedia.org/wiki/Lobry_de_Bruy
n%E2%80%93van_Ekenstein_transformati
on
http://butane.chem.uiuc.edu/pshapley/GenCh
em2/B6/2.html
Carbohydrate
http://www.unirio.br/analisedealimentos
Reactions
Oxidationaldehyde
ketone
Tollen’s reaction
http://academics.wellesley.edu/Chemistry/chem211l
ab/Orgo_Lab_Manual/Appendix/ClassificationTests
/aldehyde_ketone.html#Tollens
Carbohydrate
http://www.unirio.br/analisedealimentos
ReactionsOxidation
aldehyde
cyclic glucose
linear glucose
All five of these isomers are
present in any solution of
this sugar
glucose
Fehling’s reaction
http://butane.chem.uiuc.edu/pshapley/GenChem2
/B6/2.html
Carbohydrate
http://www.unirio.br/analisedealimentos
Reactions
http://butane.chem.uiuc.edu/pshapley/GenChem2/B6/2.html
Glucose is a polyprotic acid with 5 OH groups
Acid-Base Properties
Carbohydrate
http://www.unirio.br/analisedealimentos
ReactionsReduction
Polyol pathway
Cataract
Renal damage
Neuropathy
http://www.medbio.info/Horn/Time%205/new_diabe
tes_march_08.htm
Sinthesis of polyols
Carbohydrate
http://www.unirio.br/analisedealimentos
alcohol
ReactionsEsterefication
Proposed mechanism for covalent crosslinking between citric
acid and a polysaccharide
Hemicelluloses were extracted from wheat straw,
were added with citric acid and to produce films
Citric acid acted as a crosslinker, which was
evidenced by its decreasing effects on water solubility
and water vapor permeability, and also as a plasticizer,
which was evident from its effects on tensile propertie
Chatterjee et al. 2015
Carbohydrate
http://www.unirio.br/analisedealimentos
Cross-linking improves some properties of native starch:
thermo-mechanical shearing,
paste stability in acidic medium,
gelatinization temperature
viscosity
Some common
cross-linking
reactions of starch
using different cross-
linking reagents
Chen et al. 2015
Reactions
Carbohydrate
http://www.unirio.br/analisedealimentos
Chatterjee et al. 2015
Reactions
Carbohydrate
http://www.unirio.br/analisedealimentos
Starches
Schematic
representation of
amylose and
amylopectin
Rapidly digestible
starch (RDS), slowly
digestible starch
(SDS) and resistant
starch (RS)
SDS do not
increase the
blood glucose
level compared
to RDS
IG
Horstmann et al. 2017
Carbohydrate
http://www.unirio.br/analisedealimentos
Enzymatic degradation of amylopectin
Food control
IG
Technology
Horstmann et al. 2017
Starches
Carbohydrate
http://www.unirio.br/analisedealimentos
Starches
T0W0, control; T0W1, drought
stress (DS) treatment; T1W0,
HT treatment; T1W1,
combination of HT and DS
treatment
Lu et al. 2014
Scanning electron
micrographs of (A) potato
starch; (B) tapioca starch;
(C) corn starch; (D) rice
starch, (E) wheat starch.
Horstmann et al. 2017
Carbohydrate
http://www.unirio.br/analisedealimentos
Starches
Effective production of resistant starch using pullulanase
immobilized onto magnetic chitosan/Fe3O4 nanoparticles
In this study, pullulanase was firstly immobilized by covalent bonding onto
chitosan/Fe3O4nanoparticles or encapsulation in sol-gel after bonding onto
chitosan/Fe3O4 nanoparticles, and then the immobilized pullulanase was used for
the effective production of resistant starch (RS). The highest RS content (35.1%)
was obtained under the optimized condition of pH 4.4, enzyme concentration of
10 ASPU/g and hydrolysis time of 12 h when debranched by free pullulsanase,
indicating that RS content was significantly (p < 0.05) increased when compared to
native starch (4.3%) and autoclaved starch (12.5%). Under these conditions, the
immobilized pullulanase (10 ASPU/g dry starch) yielded higher RS content
compared to free enzyme (10 ASPU/g dry starch), especially, the pullulanse
immobilized by sol-gel encapsulation yielded the highest RS content (43.4%).
Moreover, compared to starches hydrolyzed by free pullulanase, starches
hydrolyzed by immobilized pullulanase showed a different saccharide profile of
starch hydrolysate, including a stronger peak C (MW = 5.0 × 103), as well as
exhibited an additional absorption peak around 140 °C. Reusability results
demonstrated that pullulanase immobilized by sol-gel encapsulation had the
advantages of producing higher RS content as well as better operational stability
compared to pullulanase immobilized by cross-linking. The resulting enhanced RS
content generated by the process described in this work could be used as an
adjunct in food processing industries.
Long et al. 2018
Carbohydrate
http://www.unirio.br/analisedealimentos
Starches
Long et al. 2018
Parameter Type
S1 S2 S3 S4 S5
Pasting temp (◦C) 88.00 _ _ _ _
Peak time (min) 5.67 5.87 5.60 4.60 4.67
Peak viscosity (cP) 1375.00 140.00 18.00 19.0022.00
Hold viscosity (cP) 1904.00 136.00 15.00 13.0018.00
Final viscosity (cP) 1249.00 198.00 22.00 22.0024.00
Break down (cP) 281.00 4.00 3.00 6.00 4.00
Set back (cP) 155.00 62.00 7.00 9.00 6.00
Pasting properties of native and debranched starches: pasting temperature (°C), peak time (min), peak viscosity (cP), hold viscosity (cP),
final viscosity (cP), break down (cP) and set back (cP)
S1 corresponds to raw normal maize starch; S2 corresponds to normal
maize starch treated by two autoclaving-cooling cycles; S3 to S5
correspond to normal maize starch hydrolyzed by either free pullulanase,
pullulanase immobilized by covalent bonding, or pullulanase immobilized
by sol-gel encapsulation, respectively, prior to treatment by two
autoclaving-cooling cycles.
Carbohydrate
http://www.unirio.br/analisedealimentos
Reactions Resistant starches
Long et al. 2018
SEM micrographs of native and treated
starches.(A) Typical RVA starch pasting curves of native and treated starches; (B) Differential scanning
calorimetry (DSC) thermograms of native and treated starches; (C) X-ray diffraction patterns (XRD)
of native and treated starches.
Carbohydrate
http://www.unirio.br/analisedealimentos
Gelatinisation, pasting and retrogradation of starch influenced by
heat and time, where AM is amylose and AP amylopectin
Horstmann et al. 2017
Amylose crystallises over a
period of minutes to hours, while
amylopectin retrogrades over
hours or days
process is dependent on the
amylose-amylopectin ratio
Retrogradation
collapse or disruption of
molecular order
irreversible changes in
properties
disrupting hydrogen
bonding between polymer
chains
Gelatinisation/Pasting
Reactions
Carbohydrate
http://www.unirio.br/analisedealimentos
ReactionsEffect of saccharides on sediment formation in green tea concentrate
Reducing sediment in green tea concentrate utilized for tea
production is an important process. In this study, the effect of
saccharides on sediment formation in green tea concentrate was
investigated. The results show that the amount of tea sediment
significantly decreased (31.4%–86.4%) with the addition of
fructose or sucrose and that the ratios of polyphenols and
caffeine in the sediment sharply decreased (24.1%–49.7% and
2.4%–6.2%) while the proportion of total sugars markedly
increased (20.9%–56.5%) in the sediment. Moreover, fructosyl
was found to be a highly effective functional group for preventing
sediment formation, on the basis of experimental results for a
series of sugars with different numbers of fructosyl groups. This
phenomenon was elucidated from the energies of interaction
between typical sugars, polyphenols, and caffeine calculated by
density functional theory method. Our results open new
applications for tea concentrates.
Xu et al. 2017
Carbohydrate
http://www.unirio.br/analisedealimentos
Sugars Concentration of added sugar(g/100 mL)
Catechins concentration in tea sediment (mg/mL)
Non-Gallatedcatechins
Gallated catechins Total catechins
Maltose 0 5.32 ± 1.18a 11.10 ± 1.35a 16.42 ± 2.47a
20 2.81 ± 0.65b 5.99 ± 0.72b 8.80 ± 1.24b
30 1.59 ± 0.14c 4.43 ± 0.31c 6.02 ± 0.43c
40 1.26 ± 0.11d 2.86 ± 0.53d 4.12 ± 0.65d
50 0.89 ± 0.15e 1.88 ± 0.21e 2.77 ± 0.36e
Glucose 20 2.15 ± 0.14b 6.87 ± 0.47b 9.02 ± 0.65b
30 1.63 ± 0.20c 5.11 ± 0.36c 6.73 ± 0.58c
40 1.24 ± 0.11d 3.82 ± 0.10d 5.06 ± 0.25d
50 1.13 ± 0.09d 3.55 ± 0.13d 4.67 ± 0.24d
Sucrose 20 1.11 ± 0.21b 2.82 ± 0.14b 3.93 ± 0.36b
30 0.51 ± 0.12c 1.00 ± 0.18c 1.51 ± 0.32c
40 0.18 ± 0.05d 0.28 ± 0.04d 0.46 ± 0.13d
50 0.21 ± 0.06d 0.30 ± 0.06d 0.51 ± 0.11d
Fructose 20 0.62 ± 0.08b 1.90 ± 0.12b 2.52 ± 0.23b
30 0.43 ± 0.05c 0.66 ± 0.10c 1.10 ± 0.14c
40 0.30 ± 0.06c 0.55 ± 0.04c 0.85 ± 0.10c
50 0.31 ± 0.04c 0.57 ± 0.05c 0.88 ± 0.11c
Catechin concentrations in tea sediment from tea concentrates with various
added sugars (sterilized at 90 °C for 6 min, stored at 4 °C for 14 days)
Xu et al. 2017
Sugars competitively prevent catechins from participating in tea sediment
formation and that sugars with the fructosyl group (sucrose and fructose)
inhibit participation of gallated catechins.
Reactions
Carbohydrate
http://www.unirio.br/analisedealimentos
Xu et al. 2017
Energies of glucose/fructose and EGCG/caffeine interactions.
☻Fructose dominates glucose in the competitive interaction with EGCG
or caffeine, which reduces sediment formation or turbidity.
☻ Fructose and sucrose with fructosyl are more effective at reducing the
amount of tea sediment than are maltose and glucose, with the fructosyl unit
in the sugar being a key functional group.
Reactions
Carbohydrate
http://www.unirio.br/analisedealimentos
Caramelization
Caramelization
involves both
sugar
isomerization and
sugar degradation
reactions.
Isomerization of
monosaccharides
generally starts
with enolization,
namely Lobry de
Bruyn-Alberda van
Ekenstein
transformation
reaction, followed
by sugar
degradation
reactions
General Mechanism for Thermal and Acid
Promoted Caramelization of Sucrosea
Di-D-fructose
dianhydrides
(DFAs)
Su Rez-Pereira et al. 2010
Carbohydrate
http://www.unirio.br/analisedealimentos
Maillard Reaction
http://www.photobiology.com/photoiupac2000/koldunov/
Typically, the Maillard reaction involved three stages :
the initial (condensation), the intermediate
(degradation), and the final (polymerization)
http://www.unirio.br/analisedealimentos
Carbohydrate Maillard Reaction
Proposed pathways and precursors of furan (toxicity)
Nie et al. 2013
Effect of pH, temperature and
heating time on the formation
of furan in sugar–glycine
model systems
Carbohydrate
http://www.unirio.br/analisedealimentos
Maillard Reaction
Mechanism for the Maillard reaction and caramelization during
hazelnut roasting. SUC, sucrose; GLC, glucose; FRU, fructose;
FFC, fructofuranosyl cation; 1,2-ED, 1,2-enediol; AP, Amadori
product; HP, Heyns product; 1-DG, 1-deoxyglucosone; 3-DG, 3-
deoxyglucosone 3,4-DG, 3,4-dideoxyglucosone; GO, glyoxal; MGO,
methylglyoxal; DMG, dimethylglyoxal; HMF, 5-hydroxymethyl-2-
furfural; AA, total amino acids; P, products.
Tas & Gökmen 2017
Carbohydrate
http://www.unirio.br/analisedealimentos
Zhang et al. 2013
In this research, we evaluated the impacts of six types of dietary polyphenols
on both physical and chemical characteristics of fructose caramel prepared
at either neutral or alkaline pH. Besides the potential of increasing the
browning intensity and antioxidant capacity of caramel, dietary polyphenols
were capable of influencing the amount of furfurals in caramel and most
importantly, rosmarinic acid was revealed to be a promising polyphenol to
reduce the level of harmful HMF. Chemical reactions amoung fructose,
dietary polyphenols and their thermal transformation products were found to
play an important role in the production of brown polymeric pigments and
heated-induced antioxidants in caramel. The reactions include formation of
adducts of polyphenol with sugar fragments. The findings based on the
chemical model used in this study imply interests of future research exploring
the thermal interaction between sugar and polyphenols in food systems and
how the interaction affects the sensory property and nutritional composition
of food products.
Impacts of selected dietary polyphenols on caramelization
in model systems
Carbohydrate
http://www.unirio.br/analisedealimentos
(A and B)
Comparison of
browning
intensity
amoung caramel
prepared with or
without
polyphenol
addition (CP),
polyphenol
equivalent
solution after
thermal
treatment (PE)
and calculated
sum of fructose
caramel control
and heated
polyphenol
equivalent
solution
(FE + PE)
Zhang et al. 2013
C and D Effects of sugar reactivity towards caramelization on the difference
of browning intensity between caramel prepared with polyphenol addition
and calculated sum of sugar caramel control and heated polyphenol
equivalent solution [(C) phloretin; (D) rosmarinic acid].
Carbohydrate
http://www.unirio.br/analisedealimentos
Comparison of antioxidant capacity amoung caramel prepared with
or without polyphenol addition (CP), polyphenol equivalent solution
after thermal treatment (PE) and calculated sum of fructose caramel
control and heated polyphenol equivalent solution (FE + PE) [(A)
pH = 7; (B) pH = 10
Zhang et al. 2013
http://www.unirio.br/analisedealimentos
Carbohydrate
Jiang et al. 2008
Impact of caramelisation on the glass transition temperature of several
caramelized sugars. Part I: Chemical analyses.
This study investigated the impacts of six dietary polyphenols (phloretin,
naringenin, quercetin, epicatechin, chlorogenic acid and rosmarinic acid) on
fructose caramelization in thermal model systems at either neutral or alkaline
pH. These polyphenols were found to increase the browning intensity and
antioxidant capacity of caramel. The chemical reactions in the system of sugar
and polyphenol, which include formation of polyphenol-sugar adducts, were
found to be partially responsible for the formation of brown pigments and heat-
induced antioxidants based on instrumental analysis. In addition, rosmarinic
acid was demonstrated to significantly inhibit the formation of 5-
hydroxymethylfurfural (HMF). Thus this research added to the efforts of
controlling caramelization by dietary polyphenols under thermal condition, and
provided some evidence to propose dietary polyphenols as functional
ingredients to modify the caramel colour and bioactivity as well as to lower the
amount of heat-induced contaminants such as 5-hydroxymethylfurfural (HMF).
http://www.unirio.br/analisedealimentos
Carbohydrate
Change of Tg with different holding time.
Jiang et al. 2008
Carbohydrate
http://www.unirio.br/analisedealimentos
PHONGKANPAI et al. 2006
Antioxidative activity and other characteristics of caramelization products
(CPs) from fructose or glucose solutions prepared at pHs ranging from
7.0 to 12.0 with heating at 100C for various times (0–180 min) were
investigated.ThedegradationofbothsugarsincreasedwithincreasingpHlevel
sand heatingtime(P 0.05). The intermediate degradation products and
browning intensity also increased when pH and heating time increased (P
0.05) as evidenced by the increase in A270,A285 and A420,
respectively. The reducing power and 2–2-diphenyl-1-picrylhydrazyl
radical scavenging activity of CPs were coincidental with the browning
development and the intermediate formation. Generally, CPs from
fructose showed greater antioxidative activity as shown by the higher
reducing power and scavenging effect than CPs from glucose. Therefore,
CPs from both sugars with pronounced antioxidative activity can be
prepared by heating fructose or glucose solutions at very alkaline pH for
an extended time.
Effect oh pH on antioxidative activity and other
characteristics of caramelization products
Carbohydrate
http://www.unirio.br/analisedealimentos
CHANGES IN THE REDUCING
SUGAR CONTENT OF
CARAMELIZATION PRODUCTS
FROM FRUCTOSE (A) AND
GLUCOSE (B) WITH DIFFERENT pHS
DURING HEATING AT 100C FOR
VARIOUS TIMES
(□) pH 7.0,
(▪) pH 8.0,
(▵) pH 9.0,
(▵) pH 10.0,
(○) pH 11.0 and
(●) pH 12.0.
PHONGKANPAI et al. 2006
http://www.unirio.br/analisedealimentos
Carbohydrate
Advanced glycation end products (AGEs)
The Maillard reaction
(non-enzymatic reactions
of reducing sugars with
amines) in vivo is
associated with long term
complications of diabetes,
uremia, atherosclerosis,
and Alzheimer disease
Henning et al. 2011
Degradation reactions
Carbohydrate
http://www.unirio.br/analisedealimentos
Kinetic model of acrylamide formation and elimination for mimicking Maillard reactions
Degradation reactions
http://www.unirio.br/analisedealimentos
Carbohydrate
Formation pathways of acrylamide from
asparagine. a: α-hydroxycabonyl compound
Liu et al. 2015)vvvv
Degradation reactions
Carbohydrate
http://www.unirio.br/analisedealimentos
Possible reactions polyphenols might be involved in [marked
as (1)–(7)]. Arrows pointing to polyphenols mean the reactions
steps increase acrylamide formation; arrows pointing to
intermediates mean the reaction steps reduce acrylamide
formation.
Liu et al. 2015)
Degradation reactions Role of plant polyphenols in acrylamide formation and elimination
Carbohydrate
http://www.unirio.br/analisedealimentos
Reactive carbonyl pool from various carbonyl
sources and possible reactions positions for
antioxidants (marked as (1)–(7)).
Jin et al. 2013
Relationship between antioxidants and acrylamide formation
http://www.unirio.br/analisedealimentos
ReferencesAjandouz, E.H. et al., 2008. Effects of temperature and pH on the kinetics of caramelisation, protein cross-linking and Maillard reactions in aqueous model systems.
Food Chemistry, 107(3), pp.1244–1252. Available at: http://ac-els-cdn-com.ez39.periodicos.capes.gov.br/S0308814607009910/1-s2.0-S0308814607009910-
main.pdf?_tid=86399bc2-7c9a-11e7-9c63-00000aacb35e&acdnat=1502239057_f745b142937f92aded35ec484fcf21de [Acedido Agosto 8, 2017].
Chatterjee, C., Pong, F. & Sen, A., 2015. Chemical conversion pathways for carbohydrates. Green Chem., 17(1), pp.40–71. Available at: www.rsc.org/greenchem
[Acedido Agosto 6, 2017].
Chen, Q. et al., 2015. Recent progress in chemical modification of starch and its applications. RSC Adv., 5(83), pp.67459–67474. Available at: http://pubs-rsc-
org.ez1.periodicos.capes.gov.br/en/content/articlepdf/2015/ra/c5ra10849g [Acedido Agosto 6, 2017].
Cheng, J. et al., 2014. Antioxidant-related and kinetic studies on the reduction effect of catechins and esterified catechins on acrylamide formation in a microwave
heating model system. RSC Adv., 4(82), pp.43378–43386. Available at: http://xlink.rsc.org/?DOI=C4RA04016C [Acedido Agosto 8, 2017].
Damodaran, S., Parkin, K.L. & Fennema, O.R., 2010. Quimica de Alimentos de Fennema 4.a ed. Artmed, ed., Porto Alegre.
Édira Castelo Branco de Andrade, 2015. Análise de alimentos - uma visão química da Nutrição Varela, ed., São Paulo.
Golon, A. & Kuhnert, N., Unraveling the Chemical Composition of Caramel. Available at: http://pubs-acs-org.ez1.periodicos.capes.gov.br/doi/pdf/10.1021/jf204807z
[Acedido Agosto 6, 2017].
Henning, C. et al., 2011. Molecular Basis of Maillard Amide-Advanced Glycation End Product (AGE) Formation in Vivo. The Journal of Biological Chemistry, 286(52),
pp.44350–44356. Available at: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3248017/.
Horstmann, W.S., Lynch, M.K. & Arendt, K.E., 2017. Starch Characteristics Linked to Gluten-Free Products. Foods , 6(4).
Jiang, B. et al., 2008. Impact of caramelisation on the glass transition temperature of several caramelized sugars. Part I: Chemical analyses. Journal of agricultural and
food chemistry, 56(13), pp.5138–47. Available at: http://pubs-acs-org.ez39.periodicos.capes.gov.br/doi/pdf/10.1021/jf703791e [Acedido Agosto 10, 2017].
Jin, C., Wu, X. & Zhang, Y., 2013. Relationship between antioxidants and acrylamide formation: A review. Food Research International, 51(2), pp.611–620. Available
at: http://ac-els-cdn-com.ez39.periodicos.capes.gov.br/S0963996913000070/1-s2.0-S0963996913000070-main.pdf?_tid=2b78122c-7e25-11e7-8d5e-
00000aab0f02&acdnat=1502408556_b0f5e60fabd2439c561ba479b2308eec [Acedido Agosto 10, 2017].
http://www.unirio.br/analisedealimentos
ReferencesLaroque, D. et al., 2008. Kinetic study on the Maillard reaction. Consideration of sugar reactivity. Food Chemistry, 111(4), pp.1032–1042.
Liu, Y. et al., 2015. Role of plant polyphenols in acrylamide formation and elimination. Food Chemistry, 186, pp.46–53. Available at: http://ac-els-cdn-
com.ez39.periodicos.capes.gov.br/S030881461500494X/1-s2.0-S030881461500494X-main.pdf?_tid=ee26c158-7e23-11e7-84e5-
00000aacb361&acdnat=1502408024_23a1d738a253eb7c9becdecf6cf78669 [Acedido Agosto 10, 2017].
Long, J. et al., 2018. Effective production of resistant starch using pullulanase immobilized onto magnetic chitosan/Fe<inf>3</inf>O<inf>4</inf>
nanoparticles. Food Chemistry, 239. Available at: http://ac-els-cdn-com.ez1.periodicos.capes.gov.br/S0308814617310932/1-s2.0-
S0308814617310932-main.pdf?_tid=cc432a28-7aee-11e7-9380-00000aacb361&acdnat=1502055350_3adc8ad4e8025213dc3150dcb925a73a
[Acedido Agosto 6, 2017].
Lu, H. et al., 2014. Starch composition and its granules distribution in wheat grains in relation to post‐anthesis high temperature and drought stress
treatments. Starch ‐ Stärke, 66(5–6), pp.419–428. Available at: http:https://doi.org/10.1002/star.201300070.
Nie, S. et al., 2013. Effect of pH, temperature and heating time on the formation of furan in sugar–glycine model systems. Food Science and Human
Wellness, 2(2), pp.87–92. Available at: www.sciencedirect.com [Acedido Agosto 10, 2017].
Phongkanpai, V., Benjakul, S. & Tanaka, M., 2006. Effect oh pH on antioxidative activity and other characteristics of caramelization products. Journal of Food
Biochemistry, 30(2), pp.174–186. Available at: http:https://doi.org/10.1111/j.1745-4514.2006.00053.x.
Quintas, M.A.C., Brandão, T.R.S. & Silva, C.L.M., 2007. Modelling colour changes during the caramelisation reaction. Journal of Food Engineering, 83(4),
pp.483–491. Available at: http://ac-els-cdn-com.ez39.periodicos.capes.gov.br/S0260877407002269/1-s2.0-S0260877407002269-
main.pdf?_tid=4b158622-7c9b-11e7-8eea-00000aacb361&acdnat=1502239388_5bc2b1687b104ed4c4abc3533dba4bb8 [Acedido Agosto 8, 2017].
Sengar, G. & Sharma, H.K., 2014. Food caramels: a review. Journal of Food Science and Technology, 51(9), pp.1686–1696. Available at: https://link-springer-
com.ez39.periodicos.capes.gov.br/content/pdf/10.1007%2Fs13197-012-0633-z.pdf [Acedido Agosto 10, 2017].
Suárez-Pereira, E. et al., 2010. Di-D-fructose dianhydride-enriched products by acid ion-exchange resin-promoted caramelization of D-fructose: Chemical
analyses. Journal of Agricultural and Food Chemistry, 58(3), pp.1777–1787. Available at: http://pubs-acs-
org.ez39.periodicos.capes.gov.br/doi/pdf/10.1021/jf903354y [Acedido Agosto 8, 2017].
Szwengiel, A. et al., 2018. The effect of high hydrostatic pressure treatment on the molecular structure of starches with different amylose content. Food
Chemistry, 240, pp.51–58. Available at: http://ac-els-cdn-com.ez1.periodicos.capes.gov.br/S0308814617312359/1-s2.0-S0308814617312359-
main.pdf?_tid=bc8daea6-7aed-11e7-82cd-00000aab0f02&acdnat=1502054895_aff757d9c41c59fed415e34c4d2dc70a [Acedido Agosto 6, 2017].
Tas, N.G. & Gökmen, V., 2017. Maillard reaction and caramelization during hazelnut roasting: A multiresponse kinetic study. Food Chemistry, 221, pp.1911–1922. Available at: http://ac-els-cdn-com.ez39.periodicos.capes.gov.br/S0308814616320088/1-s2.0-S0308814616320088-main.pdf?_tid=df73eefc-7c97-11e7-8c53-