EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

vanilmandelic acid
hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid

Supplier Sponsors

CAS Number: 55-10-7Picture of molecule3D/inchi
Other:2394-20-9
ECHA EINECS - REACH Pre-Reg:200-224-0
FDA UNII:0DQI268449
Nikkaji Web:J27.583B
Beilstein Number:2213227
MDL:MFCD00004235
XlogP3:-0.20 (est)
Molecular Weight:198.17470000
Formula:C9 H10 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Racemate. Register name to be changed to: 4-Hydroxy-3-methoxymandelic acid.
Category:flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:2020 hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
FLAVIS Number:08.134 (Old)
DG SANTE Food Flavourings:08.134 4-hydroxy-3-methoxymandelic acid
FEMA Number:4660 hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):55-10-7 ; HYDROXY(4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID
 
Physical Properties:
Appearance:white to pale yellow powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 132.00 °C. @ 760.00 mm Hg
Boiling Point: 421.33 °C. @ 760.00 mm Hg (est)
Flash Point: 344.00 °F. TCC ( 173.33 °C. )
logP (o/w): -0.212 (est)
Shelf Life: 12.00 month(s) or longer if stored properly.
Storage:refrigerate in tightly sealed containers.
Soluble in:
 alcohol, slightly
 water, slightly
 water, 4.267e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Description:sweet vanilla
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Adrenaline Related Compound 2 > 95%
Odor: characteristic
Use: VMA is an impurity of Epinephrine. Epinephrine is a natural neurotransmitter that is released from the adrenal medulla and activates adrenoceptors
Penta International
HYDROXY(4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID
Penta International
VANILMANDELIC ACID
Santa Cruz Biotechnology
For experimental / research use only.
4-Hydroxy-3-methoxymandelic acid ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
DL-4-Hydroxy-3-methoxymandelic acid ≥98%
TCI AMERICA
For experimental / research use only.
DL-4-Hydroxy-3-methoxymandelic Acid >99.0%(T)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavoring agents
Recommendation for vanilmandelic acid usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 120.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 5000 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 24
 average usual ppmaverage maximum ppm
baked goods: 10.0000020.00000
beverages(nonalcoholic): 5.0000010.00000
beverages(alcoholic): 10.0000020.00000
breakfast cereal: 10.0000020.00000
cheese: --
chewing gum: 5.0000010.00000
condiments / relishes: --
confectionery froastings: 10.0000020.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 10.00000100.00000
fruit ices: 10.0000020.00000
gelatins / puddings: 20.0000050.00000
granulated sugar: --
gravies: --
hard candy: 5.0000010.00000
imitation dairy: 10.0000020.00000
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: 10.0000050.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: 10.0000020.00000
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 10.0000050.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): --
Edible ices, including sherbet and sorbet (03.0): 10.00000100.00000
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000020.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 10.0000020.00000
Bakery wares (07.0): 10.0000020.00000
Meat and meat products, including poultry and game (08.0): --
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): --
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 10.0000020.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000010.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000020.00000
Ready-to-eat savouries (15.0): --
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 20.0000050.00000
 
Safety References:
European Food Safety Athority(efsa):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25
View page or View pdf

EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):55-10-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :1245
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Chemidplus:0000055107
 
References:
 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:55-10-7
Pubchem (cid):1245
Pubchem (sid):134972108
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C05584
HMDB (The Human Metabolome Database):HMDB00291
FooDB:FDB021931
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
FAO:Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
 
Potential Blenders and core components note
For Odor
anisic
para-
acetanisole
FL/FR
ortho-
anisaldehyde
FL/FR
para-
anisaldehyde
FL/FR
methyl para-anisate
FL/FR
balsamic
siam
benzoin absolute
FL/FR
benzoin absolute replacer
FL/FR
sumatra
benzoin gum
FL/FR
sumatra
benzoin resin
FL/FR
siam
benzoin resin
FL/FR
sumatra
benzoin resinoid
FL/FR
siam
benzoin resinoid
FL/FR
1-
benzoyl acetone
FL/FR
peru balsam absolute
FL/FR
peru balsam oil
FL/FR
peru balsam resinoid
FL/FR
berry
raspberry ketone methyl ether
FL/FR
caramellic
levulinic acid
FL/FR
chocolate
vanillyl ethyl ether
FL/FR
coconut
alpha-
angelica lactone
FL/FR
coumarinic
coumane
FL/FR
creamy
butyl lactate
FL/FR
para-
vanillic acid
FL/FR
para-
vanillyl alcohol
FL/FR
veratraldehyde
FL/FR
floral
acetophenone
FL/FR
para-
cresyl laurate
FL/FR
heliotropin
FL/FR
para-
methyl acetophenone
FL/FR
fruity
para-
anisyl propionate
FL/FR
ethyl methyl-para-tolyl glycidate
FL/FR
guaiacyl propionate
FL/FR
tolualdehydes (mixed o,m,p)
FL/FR
musk
omega-
pentadecalactone
FL/FR
naphthyl
2,4-
dimethyl benzaldehyde
FL/FR
nutty
nutty cyclohexenone
FL/FR
2,3,5,6-
tetramethyl pyrazine
FL/FR
phenolic
ortho-
guaiacol
FL/FR
powdery
para-
anisyl acetate
FL/FR
smoky
alpha-
ethoxy-ortho-cresol
FL/FR
spicy
para-
anisyl formate
FL/FR
4-
ethyl guaiacol
FL/FR
para-
methoxycinnamaldehyde
FL/FR
(E)-para-
methoxycinnamaldehyde
FL/FR
4-
methyl guaiacol
FL/FR
spicy acetoacetate
FL/FR
zingerone
FL/FR
sweet
vanilla bean absolute (vanilla spp.)
FL/FR
vanilla oleoresin bali
FL/FR
vanilla oleoresin bourbon
FL/FR
vanilla resinoid
FL/FR
vanilla tahitensis fruit extract
FL/FR
tonka
mint lactone
FL/FR
octahydrocoumarin
FL/FR
tropical
curcuma amada roxb. rhizome oil CO2 extract
FL/FR
vanilla
acetovanillone
FL/FR
ortho-
dimethyl hydroquinone
FL/FR
ethyl vanillin
FL/FR
ethyl vanillin isobutyrate
FL/FR
ethyl vanillin propylene glycol acetal
FL/FR
heliotropyl alcohol
FL/FR
methyl vanillate
FL/FR
propenyl guaethol
FL/FR
vanilla aromatica fruit extract
FL/FR
vanilla bean absolute (vanilla planifolia)
FL/FR
vanilla bean absolute CO2 extract (vanilla planifolia)
FL/FR
vanilla bean oil (vanilla tahitensis)
FL/FR
vanilla bean oil CO2 extract
FL/FR
vanilla extract
FL/FR
vanilla planifolia fruit extract
FL/FR
vanilla planifolia fruit water
FL/FR
vanillin
FL/FR
vanillin 2,3-butylene glycol acetal
FL/FR
vanillin propylene glycol acetal
FL/FR
vanillyl acetate
FL/FR
vanillyl isobutyrate
FL/FR
vanillylidene acetone
FL/FR
woody
4-
hydroxybenzaldehyde
FL/FR
For Flavor
No flavor group found for these
para-
anisyl propionate
FL/FR
1-
benzoyl acetone
FL/FR
coumane
FL/FR
ortho-
dimethyl hydroquinone
FL/FR
alpha-
ethoxy-ortho-cresol
FL/FR
3-(2-
furyl) acrolein
FL
glucoethyl vanillin
FL
glucovanillin
FL
guaiacyl propionate
FL/FR
heliotropyl alcohol
FL/FR
(E)-para-
methoxycinnamaldehyde
FL/FR
4-
methoxysalicylaldehyde
FL
methyl para-anisate
FL/FR
methyl vanillate
FL/FR
acidic
acidic
levulinic acid
FL/FR
anisic
para-
acetanisole
FL/FR
ortho-
anisaldehyde
FL/FR
balsamic
benzoin absolute replacer
FL/FR
sumatra
benzoin gum
FL/FR
sumatra
benzoin resin
FL/FR
siam
benzoin resin
FL/FR
siam
benzoin resinoid
FL/FR
sumatra
benzoin resinoid
FL/FR
peru balsam
FL
peru balsam absolute
FL/FR
peru balsam oil
FL/FR
peru balsam resinoid
FL/FR
vanillylidene acetone
FL/FR
berry
raspberry ketone methyl ether
FL/FR
bready
2-
propionyl thiazole
FL
cherry
heliotropin
FL/FR
para-
methoxycinnamaldehyde
FL/FR
coconut
6-
methyl coumarin
FL
octahydrocoumarin
FL/FR
creamy
alpha-
angelica lactone
FL/FR
para-
anisaldehyde
FL/FR
divanillin
FL
4-
hydroxybenzaldehyde
FL/FR
para-
methyl acetophenone
FL/FR
mint lactone
FL/FR
para-
vanillic acid
FL/FR
para-
vanillyl alcohol
FL/FR
veratraldehyde
FL/FR
dairy
butyl lactate
FL/FR
fruity
para-
anisyl acetate
FL/FR
ethyl methyl-para-tolyl glycidate
FL/FR
tolualdehydes (mixed o,m,p)
FL/FR
meaty
4-
allyl-2,6-dimethoxyphenol
FL
naphthyl
2,4-
dimethyl benzaldehyde
FL/FR
nutty
furfural acetone
FL
nutty cyclohexenone
FL/FR
2,3,5,6-
tetramethyl pyrazine
FL/FR
powdery
acetophenone
FL/FR
powdery ketone
FL
rummy
vanillyl ethyl ether
FL/FR
spicy
para-
anisyl formate
FL/FR
siam
benzoin absolute
FL/FR
spicy acetoacetate
FL/FR
zingerone
FL/FR
sweet
vanilla bean absolute (vanilla spp.)
FL/FR
vanilla oleoresin bali
FL/FR
vanilla oleoresin bourbon
FL/FR
vanilla resinoid
FL/FR
vanilla tahitensis fruit extract
FL/FR
tropical
curcuma amada roxb. rhizome oil CO2 extract
FL/FR
vanilla
acetovanillone
FL/FR
ethyl vanillin
FL/FR
ethyl vanillin isobutyrate
FL/FR
ethyl vanillin propylene glycol acetal
FL/FR
4-
methyl guaiacol
FL/FR
omega-
pentadecalactone
FL/FR
propenyl guaethol
FL/FR
vanilla aromatica fruit extract
FL/FR
vanilla bean absolute (vanilla planifolia)
FL/FR
vanilla bean absolute CO2 extract (vanilla planifolia)
FL/FR
vanilla bean oil (vanilla tahitensis)
FL/FR
vanilla bean oil CO2 extract
FL/FR
vanilla extract
FL/FR
vanilla planifolia fruit extract
FL/FR
vanilla planifolia fruit water
FL/FR
vanillin
FL/FR
vanillin 2,3-butylene glycol acetal
FL/FR
vanillin propylene glycol acetal
FL/FR
vanillyl acetate
FL/FR
vanillyl isobutyrate
FL/FR
waxy
para-
cresyl laurate
FL/FR
woody
4-
ethyl guaiacol
FL/FR
ortho-
guaiacol
FL/FR
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 benzeneacetic acid, a,4-dihydroxy-3-methoxy-
alpha-4-dihydroxy-3-methoxybenzeneacetic acid
4-hydroxy 3-methoxymandelic acid
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
DL-4-hydroxy-3-methoxy mandelic acid
4-hydroxy-3-methoxy-DL-mandelic acid
(±)-4-hydroxy-3-methoxymandelic acid
4-hydroxy-3-methoxymandelic acid
dextro,laevo-4-hydroxy-3-methoxymandelic acid
DL-4-hydroxy-3-methoxymandelic acid
4-hydroxy-3-methoxymandelicacid
4-hydroxy-3-methoxyphenyl(hydroxy)acetic acid
(4-hydroxy-3-methoxyphenyl) glycolic acid
(4-hydroxy-3-methoxyphenyl)glycolic acid
 hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
 mandelic acid, 4-hydroxy-3-methoxy-
3-methoxy-4-hydroxyphenylhydroxyacetic acid
 nibovan
 vanillinemandelic acid
 vanillomandelic acid
 vanillyl mandelic acid
 vanillylmandelic acid
(±)-vanillylmandelic acid
(±)-vanilmandelic acid
 

Articles:

PubMed:Effectiveness of green tea on weight reduction in obese Thais: A randomized, controlled trial.
PubMed:Evaluation of plasma 3,4-dihydroxyphenylacetic acid (DOPAC) and plasma 3,4-dihydroxyphenylalanine (DOPA) as tumor markers in children with neuroblastoma.
PubMed:Increased urinary HVA levels in neuroblastoma screens related to diet, not tumor.
PubMed:Energy expenditure during carbohydrate overfeeding in obese and nonobese adolescents.
PubMed:Simultaneous determination of the major acidic metabolites of catecholamines and serotonin in urine by liquid chromatography with electrochemical detection after a one-step sample clean-up on Sephadex G-10; influence of vanilla and banana ingestion.
PubMed:Diethylstilbestrol on urinary catecholamines and on food intake in castrated male rats.
PubMed:[Circadian rhythm of 3-methoxy-4-hydroxymandelic acid and 3-methoxy-4-hydroxyphenylacetic acid in the urine].
PubMed:Effects of diet on urinary excretion of MHPG in normal preadolescent boys.
PubMed:Random one-hour urine catecholamine and 4-hydroxy-3-methoxymandelic acid assays for diagnosis of pheochromocytoma.
PubMed:The effect of refeeding after semistarvation on catecholamine and thyroid metabolism.
PubMed:Urinary excretion values in 2-day food-deprived, unrestrained chimpanzees.
 
Notes:
Vanillylmandelic acid is one of the products of the catabolism of catecholamines (epinephrine, norepinephrine and dopamine). High levels of vanillylmandelic acid can indicate an adrenal gland tumor (pheochromocytoma) or another type of tumor that produces catecholamines. (WebMD) [HMDB]
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