PhytoHub: Showing entry for Vanillylmandelic acid

Vanillylmandelic acid

Identification

PhytoHub ID

PHUB001585

Name

Vanillylmandelic acid

Systematic Name

(R/S)-2-hydroxy-2-(4'-hydroxy-3'methoxyphenyl)acetic acid

Synonyms

(4-hydroxy-3-methoxyphenyl)-2-hydroxyacetic acid
(4-hydroxy-3-methoxyphenyl)-2-hydroxyethanoic acid
(4'-hydroxy-3'-methoxyphenyl)-2-hydroxyacetic acid
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethanoic acid
2-hydroxy-2-(4'-hydroxy-3'methoxyphenyl)acetic acid
2S-Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
3-Methoxy-4-hydroxymandelic acid
3'-Methoxy-4'-hydroxymandelic acid
4-hydroxy-3-methoxy-L-mandelic acid
4-hydroxy-3-methoxymandelic acid
4'-hydroxy-3'-methoxymandelic acid
Vanill mandelic acid

CAS Number

55-10-7, 2394-20-9

Average Mass

198.174

Monoisotopic Mass

198.052823422

Chemical Formula

C₉H₁₀O₅

IUPAC Name

2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

InChI Key

CGQCWMIAEPEHNQ-UHFFFAOYSA-N

InChI Identifier

InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)

SMILES

COC1=C(O)C=CC(=C1)C(O)C(O)=O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 5.16e+00 g/l
LogS (ALOGPS): -1.58
LogP (ALOGPS): 0.94
Hydrogen Acceptors: 5
Hydrogen Donors: 3
Rotatable Bond Count: 3
Polar Surface Area: 86.99000000000001
Refractivity: 47.1479
Polarizability: 18.547348727181376
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -4.128024057113833
pKa (strongest acidic): 3.113631257291667
Number of Rings: 1
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

No external links

Taxonomy as Metabolite

Family: (Poly)phenol metabolites
Class: Phenolic acid metabolites
Sub-class: Phenylacetic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Orange flavanones	Polyphenols	Flavonoids	Flavanones	Show Food Phytochemical
Black tea Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

LC-MS/MS	LC-ESI-Q	Negative	high	View Spectrum	(121.028,0.084);(136.015,0.01);(137.023,1.0);(138.031,0.012);(153.019,0.017);(153.055,0.024);(165.018,0.025);(197.045,0.212)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	medium	View Spectrum	(58.8,0.003003);(91.7,0.001001);(96.9,0.001001);(107.8,0.001001);(108.4,0.001001);(109.1,0.001001);(114.7,0.002002);(119.1,0.002002);(136.1,0.01501502);(137.0,1.0);(138.0,0.06106106);(181.9,0.002002)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	high	View Spectrum	(52.8,0.004004);(58.8,0.003003);(64.8,0.00500501);(80.8,0.01201201);(91.5,0.01001001);(92.3,0.02702703);(93.4,0.01301301);(106.8,0.00700701);(107.9,0.09209209);(109.1,0.04204204);(119.2,0.02202202);(136.0,0.17517518);(137.1,1.0)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	medium	View Spectrum	(59.2,0.00500501);(69.4,0.001001);(70.7,0.002002);(87.7,0.001001);(98.8,0.001001);(114.8,0.01301301);(120.8,0.004004);(124.8,0.003003);(136.2,0.00900901);(137.3,0.58058058);(138.0,1.0);(151.1,0.01301301);(152.9,0.02302302);(196.7,0.01601602);(197.2,0.26626627)
LC-MS/MS	LC-ESI-QTOF	Negative	high	View Spectrum	(137.0244,1.0);(138.0318,0.43943944);(197.045,0.43743744)
LC-MS/MS	LC-ESI-Q	Negative	medium	View Spectrum	(114.8,0.013);(137.3,0.58);(138.0,1.0);(151.1,0.013);(152.9,0.023);(196.7,0.016);(197.2,0.266)
LC-MS/MS	LC-ESI-Q	Negative	medium	View Spectrum	(136.1,0.015);(137.0,1.0);(138.0,0.061)
LC-MS/MS	LC-ESI-Q	Negative	high	View Spectrum	(80.8,0.012);(91.5,0.01);(92.3,0.027);(93.4,0.013);(107.9,0.092);(109.1,0.042);(119.2,0.022);(136.0,0.175);(137.1,1.0)
LC-MS/MS	LC-ESI-QTOF	Negative	low	View Spectrum	(136.0202,0.03023127);(137.0284,1.0);(138.0362,0.57091307);(153.0582,0.01223119);(197.0497,0.47781357)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(92.02949,0.01160815);(108.0224,0.01851752);(109.0327,0.01277268);(136.0202,0.04032214);(137.0284,1.0);(138.0322,0.0783186)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(53.04062,0.0184613);(81.03587,0.02290668);(92.02949,0.03129068);(93.03542,0.01230616);(108.0224,0.06016298);(109.0327,0.02159655);(136.0202,0.10738122);(137.0284,1.0)
LC-MS/MS	LC-ESI-QTOF	Negative	high	View Spectrum	(53.04062,0.05216732);(65.00468,0.01499552);(65.04086,0.01513335);(81.03587,0.05449659);(91.01914,0.03981118);(92.02949,0.0831645);(93.03542,0.01502309);(108.0224,0.2129488);(109.0327,0.0512301);(119.014,0.02238991);(136.0202,0.25779064);(137.0284,1.0)
LC-MS/MS	LC-ESI-QTOF	Negative	high	View Spectrum	(137.024,1.0);(138.032,0.439);(197.045,0.438)
LC-MS/MS	LC-ESI-QFT	Negative	medium	View Spectrum	(52.226637,0.00010326);(55.745907,0.00007002);(56.385483,0.00007361);(57.575382,0.00009874);(58.02443,0.00011245);(58.989619,0.00007844);(59.012476,0.00159628);(59.21387,0.00010343);(59.406502,0.00010783);(59.827584,0.0000755);(60.728054,0.00006627);(61.878095,0.0000722);(62.06547,0.00011041);(63.076376,0.00007482);(63.482708,0.00006846);(63.788777,0.00007749);(63.961222,0.00008839);(64.691284,0.00008625);(64.96893,0.00139023);(67.709299,0.00011788);(68.774097,0.00011848);(69.705218,0.00007451);(73.308988,0.00012854);(74.404415,0.00007707);(75.38916,0.00011147);(76.54283,0.00011386);(77.359737,0.00007272);(77.744045,0.0000984);(78.13328,0.00012191);(78.743946,0.00010145);(79.956036,0.00256067);(80.6721,0.00010905);(80.96388,0.00101749);(82.711464,0.00009773);(84.454601,0.00008968);(85.655217,0.00007023);(86.73271,0.0000714);(87.191199,0.0001124);(87.427868,0.00007255);(88.165272,0.00008497);(88.888528,0.00009872);(88.906471,0.000083);(89.308862,0.00010487);(89.405863,0.00008464);(89.797908,0.00011986);(91.369272,0.0000669);(91.517833,0.00007406);(92.207292,0.00011808);(93.033365,0.00057089);(95.177544,0.00007337);(96.356424,0.00009267);(96.958815,0.00186892);(99.184091,0.0001293);(99.92456,0.00409269);(100.907693,0.000091);(100.924648,0.00015872);(100.932423,0.00010137);(108.020429,0.00067141);(109.028007,0.00046244);(110.030063,0.00007874);(111.783443,0.00010718);(115.91954,0.00110335);(116.0705,0.00019921);(116.406157,0.00010873);(116.927384,0.00062782);(119.139861,0.00007189);(121.028278,0.0026248);(123.044,0.00244798);(124.315561,0.00012601);(125.096052,0.00294073);(125.991914,0.00012128);(127.111656,0.01898);(127.116821,0.00014671);(128.115053,0.0007839);(130.983007,0.000113);(132.483004,0.00013291);(132.905016,0.0001463);(134.194055,0.00007512);(135.044079,0.00065567);(136.015532,0.01852941);(137.013444,0.00438643);(137.023304,1.0);(138.026548,0.07616236);(138.089605,0.00008388);(138.102612,0.00013851);(139.02739,0.00533238);(141.000856,0.00007846);(141.664644,0.00012365);(141.903239,0.00007978);(142.943503,0.00013811);(145.122447,0.00006806);(146.096698,0.00008869);(147.911275,0.00010611);(148.112158,0.00137002);(148.572253,0.00012939);(149.685913,0.00007417);(150.526087,0.00007201);(151.002744,0.00042429);(151.039027,0.01371924);(152.042286,0.00043823);(153.054773,0.00447396);(156.847099,0.00009987);(159.067277,0.00011291);(162.822724,0.00009173);(162.838357,0.00007383);(163.886708,0.0000828);(164.010588,0.00009035);(164.894571,0.00008086);(166.026208,0.00035515);(171.419796,0.00015375);(173.117554,0.02136617);(174.120898,0.00213362);(174.933437,0.00012523);(174.990925,0.00007697);(175.438157,0.00008774);(177.148611,0.00011331);(177.166545,0.00008279);(178.910248,0.00015726);(179.034309,0.00007276);(179.781398,0.00011668);(180.032418,0.0002843);(182.177696,0.00010437);(183.065653,0.00145399);(185.917307,0.00009332);(189.433118,0.00011436);(193.099279,0.00318482);(194.060231,0.00065125);(194.081503,0.00007316);(194.996913,0.00013126);(197.044961,0.09571151);(198.048364,0.00947065);(198.863532,0.00011701);(199.049863,0.00040436);(199.169653,0.00073744);(199.850475,0.0001696);(200.858264,0.0023697);(201.858523,0.00030692)
LC-MS/MS	LC-ESI-QFT	Negative	high	View Spectrum	(50.050917,0.00022553);(50.664595,0.00025032);(51.293944,0.0001452);(51.779463,0.00017399);(51.893253,0.00024762);(52.581531,0.00019021);(52.832452,0.00015519);(53.071967,0.00019413);(53.136929,0.00022426);(53.268441,0.00022024);(54.473316,0.00024272);(54.636215,0.00013608);(55.471794,0.00013115);(55.863805,0.00026673);(56.714425,0.00048283);(59.012514,0.00105387);(62.303027,0.00014837);(62.68399,0.00026211);(62.764,0.00020681);(63.96106,0.00044627);(64.901023,0.00020413);(64.968944,0.00180983);(65.150972,0.0002264);(65.518744,0.00019393);(67.530618,0.00020608);(74.147517,0.00022511);(77.025862,0.0002442);(77.985262,0.00020543);(78.768708,0.00015625);(78.85324,0.00023813);(78.957841,0.00138499);(79.338873,0.00017196);(79.357427,0.0001629);(79.956065,0.00383771);(80.092093,0.00016218);(80.668203,0.00015919);(80.963791,0.00016426);(81.996014,0.00014178);(82.195341,0.00015211);(83.448151,0.00025624);(84.33354,0.00016447);(84.86231,0.00013428);(85.388542,0.00024292);(86.69325,0.00016091);(88.479049,0.00021154);(89.767454,0.00016903);(92.795528,0.00023082);(93.326537,0.0002266);(93.533133,0.00014183);(93.685842,0.00023242);(96.958801,0.00180571);(98.986722,0.00017907);(99.924608,0.0096468);(100.924832,0.00028935);(101.0869,0.00016386);(101.290419,0.00021586);(102.095995,0.00029231);(104.437584,0.00015635);(108.020514,0.00071341);(109.028102,0.00022109);(111.070949,0.00024926);(111.172786,0.00022333);(112.231373,0.00022249);(115.919527,0.00119784);(115.928146,0.00017658);(116.124175,0.00021592);(116.927258,0.00043134);(118.723574,0.00029104);(119.92436,0.00021657);(120.199704,0.00023226);(120.708136,0.00019057);(121.028383,0.00088883);(123.007578,0.00043189);(123.044035,0.00021346);(124.533136,0.00032636);(124.936256,0.0001557);(125.096078,0.00113456);(127.111705,0.01881824);(128.091145,0.00016111);(128.114746,0.00014889);(128.559644,0.00015382);(129.060038,0.0001698);(129.955133,0.00016585);(132.904875,0.0002658);(133.962005,0.00022833);(136.015514,0.02192611);(136.042539,0.00017518);(136.992166,0.00075943);(137.023291,1.0);(137.077598,0.00028806);(138.02052,0.00027671);(138.026574,0.07864945);(138.032238,0.00189478);(139.027528,0.00454493);(139.607971,0.00017534);(144.670391,0.00022551);(146.096634,0.00021496);(148.112234,0.00071298);(151.002876,0.00016398);(151.039094,0.00677501);(153.054241,0.00037212);(153.688648,0.00016745);(154.970697,0.00015936);(156.011561,0.00023365);(156.917399,0.00025878);(164.984635,0.00014923);(165.319306,0.00016531);(171.698702,0.00023392);(173.117632,0.00694246);(190.049027,0.00029925);(193.099183,0.00022326);(194.060259,0.00018323);(195.25568,0.0001466);(197.044928,0.01038989);(199.359646,0.00025086);(200.858405,0.0007259)
LC-MS/MS	LC-ESI-QFT	Negative	high	View Spectrum	(50.168267,0.00017021);(50.289556,0.00019199);(52.693128,0.00024468);(53.506352,0.00016777);(53.616854,0.00029246);(53.774427,0.00017969);(54.177086,0.00025415);(54.884061,0.00024845);(55.051775,0.00017269);(56.384823,0.00167074);(56.386033,0.00287279);(56.770256,0.00016043);(57.782177,0.00024599);(58.726227,0.00015517);(59.00911,0.00023783);(59.012515,0.00126032);(59.014105,0.00016247);(59.046524,0.00016514);(59.483944,0.00020987);(59.521136,0.00023048);(60.005645,0.00017986);(62.833113,0.00024241);(63.961073,0.00282732);(64.512291,0.00030095);(64.968894,0.00222421);(65.023007,0.00021544);(65.04891,0.00024544);(67.348903,0.00026923);(68.358053,0.0002693);(69.041259,0.00022748);(69.166607,0.00018183);(70.018213,0.0002665);(71.596289,0.00024197);(74.550181,0.00041091);(75.135285,0.0001679);(75.305447,0.00025948);(75.406158,0.00025871);(75.448831,0.00026901);(78.515678,0.0001692);(78.957755,0.00336492);(79.623236,0.00026264);(79.956007,0.0069518);(80.088583,0.00025728);(80.092044,0.00024149);(80.130609,0.00029128);(80.198897,0.00018374);(80.546632,0.00017005);(80.647969,0.00028292);(80.668233,0.00016622);(80.963785,0.00052875);(81.425788,0.00028313);(81.499955,0.00024882);(81.606874,0.00027075);(82.042634,0.00034541);(83.280128,0.00026317);(85.859375,0.00035);(85.88774,0.00016986);(87.813463,0.00028996);(89.389674,0.00027522);(90.464099,0.00024266);(91.017499,0.00023836);(91.59715,0.00018618);(93.033473,0.00056433);(93.344892,0.00024826);(95.254358,0.00017619);(96.958842,0.00217752);(97.916275,0.00025442);(99.924583,0.00861771);(100.924694,0.00031292);(104.482377,0.00028965);(106.552119,0.00027244);(107.495169,0.0001546);(108.02049,0.0035596);(109.028098,0.00055725);(111.879954,0.00017537);(112.132628,0.00017792);(115.815807,0.00031033);(115.919591,0.00042038);(116.035582,0.00022835);(117.144266,0.00026918);(121.028466,0.00027349);(121.955768,0.00024601);(123.05476,0.00033482);(125.096544,0.00036729);(126.412877,0.00024251);(126.813659,0.00022026);(127.111788,0.00398859);(134.548324,0.0002748);(134.884135,0.00027393);(136.015578,0.02416537);(137.023328,1.0);(137.539854,0.00030131);(138.026691,0.07577498);(139.027877,0.00357131);(141.000437,0.00160809);(156.011212,0.00019646);(159.595111,0.0002066);(164.497537,0.00027595);(165.830812,0.00019486);(166.327284,0.00024038);(179.42593,0.00029856);(183.491686,0.000194);(187.234917,0.00025625);(188.446899,0.00020076);(190.475572,0.0003538);(194.060501,0.00033795)
LC-MS/MS	ESI- LC-Q-TOF/MS	Negative	low	View Spectrum	(137.0244,0.999);(138.0318,0.438);(197.045,0.437)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

No food source information available of its precursor(s)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	Orange flavanones		Vanillylmandelic acid	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₉H₁₀O₅	198.052823422	Detailed Intervention Studies
	Black tea Flavan-3-ols		Vanillylmandelic acid	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₉H₁₀O₅	198.052823422	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Vanillylmandelic acid