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Copy of Beniel flavonoids April 2013

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Melanie Reichelt

on 22 April 2013

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Transcript of Copy of Beniel flavonoids April 2013

Properties and applications of citrosa R It is the trademark of Ferrer HealtTech
for the flavonoid Neohesperidin DC 1. Origin and production
2. Solubility
3. Stability
4. Regulatory status
5. Sensory properties flavour enhancer
sweetness enhancer
masking agen Origin and Production
Discovered in 1963 (Horowitz & Gentili)
Study of taste-structure relationships
Hydrogination of neohesperidin, a bitter flavonoid from citrus aurantium
Taste shift after hydrogenation After Extraction and Purification
Neohesperidin After Hydrogenation
Neohesperidin DC Albedo
(flavonoids) Flavedo
(essential oil) World wide collection
Own plantation
Research flavonoid accumulation in the plant in collaboration with research institution (IRTA) Solubility in water
0.5 g/L at 25 ºC
65% at 80 ºC Solubility is not a limitation for use in food and beverages Stability
Shelf life over 3 years at room temperature without any sign of decomposition
Photo stability tested according to ICH guidelines
Slightly hygroscopic
takes up to 15% by weight
water forms part of the crystal structure
Crystal structure changes from monociclic21 to amorfous when becomes anhydrous Remaining NHDC % after 12 month storage at 20ºC pH Data taken from: Canales et al. (1993), J Food Sci, 57, 589-591 pH
7 Half life 20ºC (yr)
7.0 Half life 60ºC (d)
9.9 Aqueous model systems NHDC L-rhamnose + D-glucose phloroglucinol phenyl acetic acid NHDC Hesperitin dihydrochalcone L-rhamnose + D-glucose Acid Hydrolisis Alkaline Hydrolisis Enhanced in:
Alkaline solution Regulatory situation Food Citrosa is approved as flavour ingredient by the Fema Expert Panel since September 1993 with Fema Nr 3811.
See publication of Gras Flavoring substances for use limits.
See list of countries that follow the Fema Gras regulation. Citrosa is approved as flavour ingredient in Japan without use restrictions. Citrosa is approved as flavour ingredient by EFSA according to EU Regulation 872/2012 with Flavis Number 16.061.
See EU Reg 872/2012 for use limits (Table 1). EU USA JAPAN In the EU, Citrosa is also approved as an intensive sweetener under Directive 94/35/EC.
Implemented in all EU member states + Turkey + Switzerland
Mandatory label declaration
High maximum use limits
In practice:
< 3ppm: use and declaration as flavour
>3ppm use and declaration as intensive sweetener Citrosa has a monography in the European Pharmacopeia. Approved as excipient in pharma.
Citrosa is approved under the INCI system for cosmetic ingredients.
Citrosa is approved in feedstuffs both in the EU (1991,1993) and USA (AAFCO-FCA, 2005). Regulatory others Flavor enhancer sweetness
enhancer masking agent Mouthfeel
Creaminess Sweetness
Synergy Flavours notes
Fruity flavours
Roasted notes
Bitterness Sweetening intensity ca 1700 times sugar Time vs Intensity curve Synergies Source: Leatherhead Food RA Ingredients Handbook Data taken from: Schiffman et al. (1995), Brain Res Bull, 38, 105-120 Flavour intensity Bitterness Mouthfeel Data taken from Lindley et al. (1993) J Food Sci, 58, 592-594 Data taken from Lindley et al. (1993) J Food Sci, 58, 592-594 Data taken from Lindley et al. (1993) J Food Sci, 58, 592-594 Flavour intensity Bitterness Duration Mouthfeel Bitterness Bulk sugar substitution Thank you Production of citrus and fruit Bioflavonoids Sweet orange (citrus sinensis)

Bitter orange (citrus aurantium)

Grape fruit (citrus paradisi)

Apple (malus domestica)

Olive leaf (Olea europa) Hesperidin

Neohesperidin dc

Phloretin Eriodictyol



Olews 40%
Bonolive Total surface 50.000 m2
Extraction 100 m3
Reaction 40 m3
ISO 9001 and 14001 (1996)
DMF Diosmin (2007)
CEP (Certificate E.Ph.2009)
FSSC 22000 Certificate (2012=
Halal and Kosher certificates Schiffman et al. (1995), Brain Res Bull, 38, 105-120 Schiffman et al. (1995), Brain Res Bull, 38, 105-120 Schiffman et al. (1995), Brain Res Bull, 38, 105-120 Flavanone
Present in Yerba Santa
Produced by FHT from sweet orange, hemisynthesis => artificial flavour
Fema Gras: 4228: homoeriodictyol sodium salt
No sweetness, neutral.
Max dosage. not specified (FEMA)
Recommended dosage. 50ppm (metallic notes and bitternes blocker)
Solubility: 5% in PG at 60%
High stability low pH and T

US Patent 2002/0188019 from May 8, 2002: Use of hydroxyflavones for masking bitter taste.
Bayer => symrise
covers both homoeriodictyol and its salts
Symrise produces HED as a Yerba Santa extract. Citrus flavonoid
Industrially available.
Produced by FHT as natural flavour.
FHT is currently preparing the Fema Gras filling.
SP: negligible in water (neutral)
recommended dosage: 20-40 ppm
solubility: 5% in PG ag 60 ºC
High stability at low pH and vs T

Was removed in 2011 from Symrise's patent application 2002/0188019 Measuring antibittering effect

Based on the protocol described in J.Agric.Food Chem 2006, 54, 8574 - 8579 and Chem. Percept (2008) 1:58 - 77

Water + 500 ppm caffein + 10, 50, 100, 200, 500 ppm of compound to be tested

Compare equibitterness with absolute scale of water + 75, 100, 125, 150, 175, 200, 250, 300, 400, 500 ppm of caffein

Bitternes suppresion expressed in % and calculated as (500ppm - equibitter concentration)/ 500ppm

This work was repeate for the two other activators of the bitterness receptors, respectively 5000 ppm of paracetamol/acetominophen and 250 ppm of quinine Homoeriodictyol Naringenin Flavonoids are a group of polyphenolic compounds present in all fruits and vegetables. Citrus flavonoids are present in all citrus species. cbc is an extract from bitter orange. Ferrer Health Tech produces cbc in its facility in Murcia (Spain) as an extract from the whole fruit allowing consumers to recover all benefits of the original fruit.

cbc - a unique ingredient
We all know we should eat several pieces of fruit per day. However, the rhythm of everyday life often keeps us from doing so. This is even more the case for citrus fruits, where the citrus flavonoids, are largely concentrated in the peel and not in the juice. This is not suprising since citrus flavonoids are not water soluble.

Hence consumers miss the lion part of the healthy ingredients in citrus fruits. Ferrer HealthTech produces cbc as an extract of the whole fruit with propietary process and standardises the citrus flavonoid content to 45%. Cbc comprises 10 different citrus flavonoids, whereof naringin is the most important one with 25% of the extract. The complex of these 10 citrus flavonoids is highly water soluble. cbc i unique because it is perfectly water soluble and natural. cbc is the ideal ingredient to enable food producers to reincorporate the health benefits of the whole fruit into their food matrices. Naringin is a flavanone glycoside. It is a major flavonoid in grapefruit and gives the grapefruit juice its bitter taste.

It is metabolized to the flavanone naringenin in humans. Both naringenin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Naringin It is classified as a phytochemical, which is a naturally occurring plant compound with potential nutritional benefits.

Specifically, naringin is a water soluble flavonoid. It has been studied for its potential antioxidant and anti-carcinogenic properties, as well as its effects on enzyme activity in the digestive tract. Supplements containing naringin are typically used to enhance the effects of other drugs.

Regulatory R. 872/2012 List of flavoring substances chemically defined. Flavis 16.058 Dihydrochalcone
Origin: apple and grapefruit
Reg. Flavis 16.109 and FEMA 16.109
Available both natural and artificial.
SP: negligible in water (neutral)
max dosage drinks: 300 ppm (FEMA)
recommended dosage: 20-40 ppm
solubility: 5% in PG ag 60 ºC
High stability at low pH and vs T Phloretin Thank You
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